Novel n-aryltetrahydrophthalimide compounds

ABSTRACT

N-aryltetrahydrophthalimide compounds of the general formula I &lt;IMAGE&gt; I  where n, R1, Y, R2 and R3 have the meanings stated in the claims and description, and a method for controlling undesirable plant growth.

This application is a continuation of application Ser. No. 315,128, filed on Feb. 24, 1989 now abandoned.

The present invention relates to N-phenyltetrahydrophthalimide compounds of the general formula I ##STR2## where the substituents and indices have the following meanings: n is 0 or 1, R¹ is hydrogen or halogen, Y is --O--, --S--, --CH₂ --, --S--CR⁴ R⁵ --, --O--CR⁴ R⁵ -- or --CH₂ --CR⁴ R⁵ --, R⁴ and R⁵ independently of one another being hydrogen or C₁ -C₃ -alkyl, R² is hydrogen or C₁ -C₃ -alkyl, R³ is a saturated or monounsaturated 5-membered or 6-membered ring which has an oxygen or sulfur atom in the ring and may be monosubstituted to trisubstituted by C₁ -C₃ -alkyl, or R³ is phenyl which is unsubstituted or monosubstituted to trisubstituted by C₁ - or C₂ -alkyl, halogen, methoxy, nitro and/or cyano, and if n is 0 and Y is --CH₂ --, --CH₂ --CR⁴ R⁵ -- or --S--CR⁴ R⁵ --, R³ may furthermore be hydrogen, C₁ -C₅ -alkyl, C₃ - or C₄ -alkenyl, C₃ - or C₄ -alkynyl, C₁ -C₄ -haloalkyl, C₃ - or C₄ -haloalkenyl, C₁ - or C₂ -alkoxy-C₁ - or C₂ -alkyl, C₁ - or C₂ -alkoxy-C₁ - or C₂ -alkoxy-C₁ - or C₂ -alkyl or C₁ -C₆ -alkoxycarbonyl-substituted C₁ -C₃ -alkyl.

The present invention furthermore relates to a method for controlling undesirable plant growth and herbicides which contain these compounds.

N-aryl-substituted tetrahydrophthalimides having a herbicidal action are known. For example, EP-A-170 191 describes tetrahydrophthalimides, but their activity is unsatisfactory at low application rates.

It is an object of the present invention to provide appropriately improved tetrahydrophthalimide compounds.

We have found that this object is achieved in that the N-aryltetrahydrophthalimide compounds of the formula I which were defined at the outset have an advantageous herbicidal action, particularly by the postemergence method, and are selective with respect to a number of crops. Where these compounds are capable of forming stereoisomers, the invention relates to all isomers.

The compounds I are obtained, for example, by first reacting an appropriately substituted aniline of the formula II in a conventional manner in an inert organic solvent with an N-alkylating compound Z--(CHR²)_(n) R³ to give the aniline derivative III and then condensing this in an inert organic solvent with 3,4,5,6-tetrahydrophthalic anhydride to give the N-aryltetrahydrophthalimide I. ##STR3##

The radical Z in the alkylating reagent is a nucleophilic leaving group conventionally used in organic chemistry, such as halogen, eg. chlorine, bromine and iodine, or sulfonyl, such as toluenesulfonyl or mesyl.

The alkylation is carried out in a conventional manner at up to 200° C., preferably from 0° to 150° C., in an aprotic polar solvent (eg. acetone, acetonitrile or dimethylformamide), in the presence of a base (eg. potassium carbonate, sodium hydroxide or sodium hydride).

The condensation of the aniline derivative III with 3,4,5,6-tetrahydrophthalic anhydride is carried out in a protic solvent, such as acetic acid, propionic acid or isobutyric acid, or in an aprotic solvent, such as toluene, xylene or dimethylformamide. The reaction is carried out, as a rule, at from 25° to 200° C., preferably from 70° to 140° C. When an aprotic solvent is used, it is advisable to remove the water continuously.

However, the compounds I are also obtained if an amine II if first condensed with 3,4,5,6-tetrahydrophthalic anhydride to give the N-phenyltetrahydrophthalimide IV, and the latter is then reacted with an N-alkylating compound Z--(CHR²)_(n) R³ to give I. ##STR4##

These reactions are carried out under conditions similar to those described above.

The required compounds II are prepared in a conventional manner: S. Gabriel et al., Chem. Ber. 12 (1879), 600; W. A. Sexton, J. Chem. Soc. 1939, 470; D. R. Shridar et al., Synthesis 1982, 986; Sandmeyer, Chem. Ber. 19 (1886), 2656, and D. R. Shridar et al., Indian J. Chem. 24B (1985), 1263.

For the use of the compounds I in accordance with regulations, the following radicals are preferred substituents.

Halogen as used above is fluorine, chlorine or bromine, halogen radicals R¹ preferably being fluorine.

Alkyl includes branched and straight-chain radicals, eg. methyl, ethyl, n-propyl and isopropyl.

The alkenyl and alkynyl radicals may likewise be branched or straight-chain. Examples of alkenyl radicals in formula I are allyl, 2-propenyl, 2-butenyl, 3-butenyl and 2-isobutenyl, in particular allyl and 2-butenyl, and alkynyl radicals are, as a rule, propargyl, 2-butynyl or 3-butynyl.

The five-membered or six-membered heterocyclic ring of the formula I is preferably a hydrogenated or partially hydrogenated furan, thiophene, pyran or thiopyran ring.

Phenyl preferably includes the unsubstituted and monosubstituted derivatives, eg. chlorophenyl, methylphenyl and methoxyphenyl.

The N-substituted tetrahydrophthalimides are obtainable from 3,4,5,6-tetrahydrophthalic anhydride and an appropriate aniline of the formula III, for example in a solvent at from 20° to 200° C., preferably from 40° to 150° C. Suitable solvents are, for example, lower alkanoic acids, such as glacial acetic acid or propionic acid, or aprotic solvents, such as toluene or xylene, in the presence of an acidic catalyst, for example an aromatic sulfonic acid.

Preferred compounds I are those in which R¹ is hydrogen or fluorine, R² and R³ are each hydrogen or methyl, R⁴ is hydrogen and R⁵ is 2- or 3-tetrahydrofuryl, 2- or 3-tetrahydrothienyl, 2- or 3- or 4-tetrahydropyranyl, 2-, 3- or 4-tetrahydrothiopyranyl, 5,6-dihydro-2H-pyranyl or 5,6-dihydro-2H-thiopyranyl.

Particularly active novel compounds are listed in Tables I, II, IIa, III, IIIa, IV, IVa, V and VI below.

                  TABLE I                                                          ______________________________________                                          ##STR5##                                                                      R.sup.1                                                                               R.sup.2                                                                               R.sup.3          R.sup.4                                                                             R.sup.5                                    ______________________________________                                         H      H                                                                                      ##STR6##        H    H                                          F      H                                                                                      ##STR7##        H    H                                          H      CH.sub.3                                                                               ##STR8##        H    H                                          F      CH.sub.3                                                                               ##STR9##        H    H                                          H      H                                                                                      ##STR10##       H    H                                          F      H                                                                                      ##STR11##       H    H                                          H      CH.sub.3                                                                               ##STR12##       H    H                                          F      CH.sub.3                                                                               ##STR13##       H    H                                          H      H                                                                                      ##STR14##       H    H                                          F      H                                                                                      ##STR15##       H    H                                          H      CH.sub.3                                                                               ##STR16##       H    H                                          F      CH.sub.3                                                                               ##STR17##       H    H                                          H      H                                                                                      ##STR18##       H    H                                          F      H                                                                                      ##STR19##       H    H                                          H      CH.sub.3                                                                               ##STR20##       H    H                                          F      CH.sub.3                                                                               ##STR21##       H    H                                          H      H                                                                                      ##STR22##       H    H                                          F      H                                                                                      ##STR23##       H    H                                          H      CH.sub.3                                                                               ##STR24##       H    H                                          F      CH.sub.3                                                                               ##STR25##       H    H                                          H      H                                                                                      ##STR26##       CH.sub.3                                                                            H                                          F      H                                                                                      ##STR27##       CH.sub.3                                                                            H                                          H      CH.sub.3                                                                               ##STR28##       CH.sub.3                                                                            H                                          F      CH.sub.3                                                                               ##STR29##       CH.sub.3                                                                            H                                          H      H                                                                                      ##STR30##       CH.sub.3                                                                            CH.sub.3                                   F      H                                                                                      ##STR31##       CH.sub.3                                                                            CH.sub.3                                   H      CH.sub.3                                                                               ##STR32##       CH.sub.3                                                                            CH.sub.3                                   F      CH.sub.3                                                                               ##STR33##       CH.sub.3                                                                            CH.sub.3                                   H      H                                                                                      ##STR34##       H    H                                          F      H                                                                                      ##STR35##       H    H                                          H      CH.sub.3                                                                               ##STR36##       H    H                                          F      CH.sub.3                                                                               ##STR37##       H    H                                          H      H                                                                                      ##STR38##       CH.sub.3                                                                            H                                          F      H                                                                                      ##STR39##       CH.sub.3                                                                            H                                          H      CH.sub.3                                                                               ##STR40##       CH.sub.3                                                                            H                                          F      CH.sub.3                                                                               ##STR41##       CH.sub.3                                                                            H                                          H      H                                                                                      ##STR42##       CH.sub.3                                                                            CH.sub.3                                   F      H                                                                                      ##STR43##       CH.sub.3                                                                            CH.sub.3                                   H      CH.sub.3                                                                               ##STR44##       CH.sub.3                                                                            CH.sub.3                                   F      CH.sub.3                                                                               ##STR45##       CH.sub.3                                                                            CH.sub.3                                   H      H                                                                                      ##STR46##       H    H                                          F      H                                                                                      ##STR47##       H    H                                          H      CH.sub.3                                                                               ##STR48##       H    H                                          F      CH.sub.3                                                                               ##STR49##       H    H                                          H      H                                                                                      ##STR50##       CH.sub.3                                                                            H                                          F      H                                                                                      ##STR51##       CH.sub.3                                                                            H                                          H      CH.sub.3                                                                               ##STR52##       CH.sub.3                                                                            H                                          F      CH.sub.3                                                                               ##STR53##       CH.sub.3                                                                            H                                          H      H                                                                                      ##STR54##       H    H                                          F      H                                                                                      ##STR55##       H    H                                          H      CH.sub.3                                                                               ##STR56##       H    H                                          F      CH.sub.3                                                                               ##STR57##       H    H                                          H      H                                                                                      ##STR58##       CH.sub.3                                                                            H                                          F      H                                                                                      ##STR59##       CH.sub.3                                                                            H                                          H      CH.sub.3                                                                               ##STR60##       CH.sub.3                                                                            H                                          F      CH.sub.3                                                                               ##STR61##       CH.sub.3                                                                            H                                          H      H                                                                                      ##STR62##       CH.sub.3                                                                            CH.sub.3                                   F      H                                                                                      ##STR63##       CH.sub.3                                                                            CH.sub.3                                   H      CH.sub.3                                                                               ##STR64##       CH.sub.3                                                                            CH.sub.3                                   F      CH.sub.3                                                                               ##STR65##       CH.sub.3                                                                            CH.sub.3                                   H      H                                                                                      ##STR66##       H    H                                          F      H                                                                                      ##STR67##       H    H                                          H      CH.sub.3                                                                               ##STR68##       H    H                                          F      CH.sub.3                                                                               ##STR69##       H    H                                          H      H                                  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##STR74##       CH.sub.3                                                                            CH.sub.3                                   F      H                                                                                      ##STR75##       CH.sub.3                                                                            CH.sub.3                                   H      CH.sub.3                                                                               ##STR76##       CH.sub.3                                                                            CH.sub.3                                   F      CH.sub.3                                                                               ##STR77##       CH.sub.3                                                                            CH.sub.3                                   H      H                                                                                      ##STR78##       CH.sub.3                                                                            CH.sub.3                                   F      H                                                                                      ##STR79##       CH.sub.3                                                                            CH.sub.3                                   H      CH.sub.3                                                                               ##STR80##       CH.sub.3                                                                            CH.sub.3                                   F      CH.sub.3                                                                               ##STR81##       CH.sub.3                                                                            CH.sub.3                                   H      H                                                                                      ##STR82##       H    H                                          F      H                                  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##STR88##       CH.sub.3                                                                            H                                          F      CH.sub.3                                                                               ##STR89##       CH.sub.3                                                                            H                                          H      H                                                                                      ##STR90##       CH.sub.3                                                                            CH.sub.3                                   F      H                                                                                      ##STR91##       CH.sub.3                                                                            CH.sub.3                                   H      CH.sub.3                                                                               ##STR92##       CH.sub.3                                                                            CH.sub.3                                   F      CH.sub.3                                                                               ##STR93##       CH.sub.3                                                                            CH.sub.3                                   H      H                                                                                      ##STR94##       H    H                                          F      H                                                                                      ##STR95##       H    H                                          H      CH.sub.3                                                                               ##STR96##       H    H                                          F      CH.sub.3                                                                               ##STR97##       H    H                                          H      H                                  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##STR102##      H    H                                          F      H                                                                                      ##STR103##      H    H                                          H      CH.sub.3                                                                               ##STR104##      H    H                                          F      CH.sub.3                                                                               ##STR105##      H    H                                          H      H                                                                                      ##STR106##      H    H                                          F      H                                                                                      ##STR107##      H    H                                          H      CH.sub.3                                                                               ##STR108##      H    H                                          F      CH.sub.3                                                                               ##STR109##      H    H                                          H      H                                                                                      ##STR110##      H    H                                          F      H                                                                                      ##STR111##      H    H                                          H      CH.sub. 3                                                                              ##STR112##      H    H                                          F      CH.sub.3                                                                               ##STR113##      H    H                                          H      H                                                                                      ##STR114##      H    H                                          F      H                                                                                      ##STR115##      H    H                                          H      CH.sub.3                                                                               ##STR116##      H    H                                          F      CH.sub.3                                                                               ##STR117##      H    H                                          H      H                                                                                      ##STR118##      H    H                                          F      H                                                                                      ##STR119##      H    H                                          H      CH.sub.3                                                                               ##STR120##      H    H                                          F      CH.sub.3                                                                               ##STR121##      H    H                                          H      H                                                                                      ##STR122##      CH.sub.3                                                                            H                                          F      H                                                                                      ##STR123##      CH.sub.3                                                                            H                                          H      CH.sub.3                                                                               ##STR124##      CH.sub.3                                                                            H                                          F      CH.sub.3                                                                               ##STR125##      CH.sub.3                                                                            H                                          H      H                                                                                      ##STR126##      CH.sub.3                                                                            CH.sub.3                                   F      H                                                                                      ##STR127##      CH.sub.3                                                                            CH.sub.3                                   H      CH.sub.3                                                                               ##STR128##      CH.sub.3                                                                            CH.sub.3                                   F      CH.sub.3                                                                               ##STR129##      CH.sub.3                                                                            CH.sub.3                                   H      H                                                                                      ##STR130##      H    H                                          F      H                                                                                      ##STR131##      H    H                                          H      CH.sub.3                                                                               ##STR132##      H    H                                          F      CH.sub.3                                                                               ##STR133##      H    H                                          H      H                                                                                      ##STR134##      CH.sub.3                                                                            H                                          F      H                                                                                      ##STR135##      CH.sub.3                                                                            H                                          H      CH.sub.3                                                                               ##STR136##      CH.sub.3                                                                            H                                          F      CH.sub.3                                                                               ##STR137##      CH.sub.3                                                                            H                                          H      H                                                                                      ##STR138##      CH.sub.3                                                                            CH.sub.3                                   F      H                                                                                      ##STR139##      CH.sub.3                                                                            CH.sub.3                                   H      CH.sub.3                                                                               ##STR140##      CH.sub.3                                                                            CH.sub.3                                   F      CH.sub.3                                                                               ##STR141##      CH.sub.3                                                                            CH.sub.3                                   H      H                                                                                      ##STR142##      H    H                                          F      H                                                                                      ##STR143##      H    H                                          H      CH.sub.3                                                                               ##STR144##      H    H                                          F      CH.sub.3                            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                   H                                          H      H                                                                                      ##STR150##      H    H                                          F      H                                                                                      ##STR151##      H    H                                          H      CH.sub.3                                                                               ##STR152##      H    H                                          F      CH.sub.3                                                                               ##STR153##      H    H                                          H      H                                                                                      ##STR154##      CH.sub.3                                                                            H                                          F      H                                                                                      ##STR155##      CH.sub.3                                                                            H                                          H      CH.sub.3                                                                               ##STR156##      CH.sub.3                                                                            H                                          F      CH.sub.3                                                                               ##STR157##      CH.sub.3                                                                            H                                          H      H                                                                                      ##STR158##      CH.sub.3                                                                            CH.sub.3                                   F      H                                                                                      ##STR159##      CH.sub.3                                                                            CH.sub.3                                   H      CH.sub.3                                                                               ##STR160##      CH.sub.3                                                                            CH.sub.3                                   F      CH.sub.3                                                                               ##STR161##      CH.sub.3                                                                            CH.sub.3                                   H      H                                                                                      ##STR162##      H    H                                          F      H                                                                                      ##STR163##      H    H                                          H      CH.sub.3                                                                               ##STR164##      H    H                                          F      CH.sub.3                                                                               ##STR165##      H    H                                          H      H                                                                                      ##STR166##      CH.sub.3                                                                            H                                          F      H                                                                                      ##STR167##      CH.sub.3                                                                            H                                          H      CH.sub.3                                                                               ##STR168##      CH.sub.3                                                                            H                                          F      CH.sub.3                                                                               ##STR169##      CH.sub.3                                                                            H                                          H      H                                                                                      ##STR170##      CH.sub.3                                                                            CH.sub.3                                   F      H                                                                                      ##STR171##      CH.sub.3                                                                            CH.sub.3                                   H      CH.sub.3                                                                               ##STR172##      CH.sub.3                                                                            CH.sub.3                                   F      CH.sub.3                                                                               ##STR173##      CH.sub.3                                                                            CH.sub.3                                   H      H                                                                                      ##STR174##      CH.sub.3                                                                            CH.sub.3                                   F      H                                                                                      ##STR175##      CH.sub.3                                                                            CH.sub.3                                   H      CH.sub.3                                                                               ##STR176##      CH.sub.3                                                                            CH.sub.3                                   F      CH.sub.3                                                                               ##STR177##      CH.sub.3                                                                            CH.sub.3                                   H      H                                                                                      ##STR178##      H    H                                          F      H                                                                                      ##STR179##      H    H                                          H      CH.sub.3                                                                               ##STR180##      H    H                                          F      CH.sub.3                                                                               ##STR181##      H    H                                          H      H                                                                                      ##STR182##      CH.sub.3                                                                            H                                          F      H                                                                                      ##STR183##      CH.sub.3                                                                            H                                          H      CH.sub.3                                                                               ##STR184##      CH.sub.3                                                                            H                                          F      CH.sub.3                                                                               ##STR185##      CH.sub.3                                                                            H                                          H      H                                                                                      ##STR186##      CH.sub.3                                                                            CH.sub.3                                   F      H                                                                                      ##STR187##      CH.sub.3                                                                            CH.sub.3                                   H      CH.sub.3                                                                               ##STR188##      CH.sub.3                                                                            CH.sub.3                                   F      CH.sub.3                                                                               ##STR189##      CH.sub.3                                                                            CH.sub.3                                   H      H                                                                                      ##STR190##      H    H                                          F      H                                                                                      ##STR191##      H    H                                          H      CH.sub.3                                                                               ##STR192##      H    H                                          F      CH.sub.3                                                                               ##STR193##      H    H                                          H      H                                                                                      ##STR194##      CH.sub.3                                                                            H                                          F      H                                                                                      ##STR195##      CH.sub.3                                                                            H                                          H      CH.sub.3                                                                               ##STR196##      CH.sub.3                                                                            H                                          F      CH.sub.3                                                                               ##STR197##      CH.sub.3                                                                            H                                          H      H                                                                                      ##STR198##      H    H                                          F      H                                                                                      ##STR199##      H    H                                          H      CH.sub.3                                                                               ##STR200##      H    H                                          F      CH.sub.3                                                                               ##STR201##      H    H                                          H      H                                                                                      ##STR202##      CH.sub.3                                                                            H                                          F      H                                                                                      ##STR203##      CH.sub.3                                                                            H                                          H      CH.sub.3                                                                               ##STR204##      CH.sub.3                                                                            H                                          F      CH.sub.3                                                                               ##STR205##      CH.sub.3                                                                            H                                          H      H                                                                                      ##STR206##      CH.sub.3                                                                            CH.sub.3                                   F      H                                                                                      ##STR207##      CH.sub.3                                                                            CH.sub.3                                   H      CH.sub.3                                                                               ##STR208##      CH.sub.3                                                                            CH.sub.3                                   F      CH.sub.3                                                                               ##STR209##      CH.sub.3                                                                            CH.sub.3                                   H      H                                                                                      ##STR210##      H    H                                          F      H                                                                                      ##STR211##      H    H                                          H      CH.sub.3                                                                               ##STR212##      H    H                                          F      CH.sub.3                                                                               ##STR213##      H    H                                          H      H                                                                                      ##STR214##      H    H                                          F      H                                                                                      ##STR215##      H    H                                          H      CH.sub.3                                                                               ##STR216##      H    H                                          F      CH.sub.3                                                                               ##STR217##      H    H                                          H      H                                                                                      ##STR218##      H    H                                          F      H                                                                                      ##STR219##      H    H                                          H      CH.sub.3                                                                               ##STR220##      H    H                                          F      CH.sub.3                                                                               ##STR221##      H    H                                          ______________________________________                                    

                  TABLE II                                                         ______________________________________                                          ##STR222##                                                                    R.sup.1 R.sup.2                                                                               R.sup.3          R.sup.4                                                                             R.sup.5                                   ______________________________________                                         H       H                                                                                      ##STR223##      H    H                                         F       H                                                                                      ##STR224##      H    H                                         H       CH.sub.3                                                                               ##STR225##      H    H                                         F       CH.sub.3                                                                               ##STR226##      H    H                                         H       H                                                                                      ##STR227##      H    H                                         F       H                                                                                      ##STR228##      H    H                                         H       CH.sub.3                                                                               ##STR229##      H    H                                         F       CH.sub.3                                                                               ##STR230##      H    H                                         H       H                                                                                      ##STR231##      H    H                                         F       H                                                                                      ##STR232##      H    H                                         H       CH.sub.3                                                                               ##STR233##      H    H                                         F       CH.sub.3                                                                               ##STR234##      H    H                                         H       H                                                                                      ##STR235##      H    H                                         F       H                                                                                      ##STR236##      H    H                                         H       CH.sub.3                                                                               ##STR237##      H    H                                         F       CH.sub.3                                                                               ##STR238##      H    H                                         H       H                                                                                      ##STR239##      H    H                                         F       H                                                                                      ##STR240##      H    H                                         H       CH.sub.3                                                                               ##STR241##      H    H                                         F       CH.sub.3                                                                               ##STR242##      H    H                                         H       H                                                                                      ##STR243##      CH.sub.3                                                                            H                                         F       H                                                                                      ##STR244##      CH.sub.3                                                                            H                                         H       CH.sub.3                                                                               ##STR245##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR246##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR247##      CH.sub.3                                                                            CH.sub.3                                  F       H                                                                                      ##STR248##      CH.sub.3                                                                            CH.sub.3                                  H       CH.sub.3                                                                               ##STR249##      CH.sub.3                                                                            CH.sub.3                                  F       CH.sub.3                                                                               ##STR250##      CH.sub.3                                                                            CH.sub.3                                  H       H                                                                                      ##STR251##      H    H                                         F       H                                                                                      ##STR252##      H    H                                         H       CH.sub.3                                                                               ##STR253##      H    H                                         F       CH.sub.3                                                                               ##STR254##      H    H                                         H       H                                                                                      ##STR255##      CH.sub.3                                                                            H                                         F       H                                                                                      ##STR256##      CH.sub.3                                                                            H                                         H       CH.sub.3                                                                               ##STR257##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR258##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR259##      CH.sub.3                                                                            CH.sub.3                                  F       H                                                                                      ##STR260##      CH.sub.3                                                                            CH.sub.3                                  H       CH.sub.3                                                                               ##STR261##      CH.sub.3                                                                            CH.sub.3                                  F       CH.sub.3                                                                               ##STR262##      CH.sub.3                                                                            CH.sub.3                                  H       H                                                                                      ##STR263##      H    H                                         F       H                                                                                      ##STR264##      H    H                                         H       CH.sub.3                                                                               ##STR265##      H    H                                         F       CH.sub.3                                                                               ##STR266##      H    H                                         H       H                                                                                      ##STR267##      CH.sub. 3                                                                           H                                         F       H                                                                                      ##STR268##      CH.sub.3                                                                            H                                         H       CH.sub.3                                                                               ##STR269##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR270##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR271##      H    H                                         F       H                                                                                      ##STR272##      H    H                                         H       CH.sub.3                                                                               ##STR273##      H    H                                         F       CH.sub.3                                                                               ##STR274##      H    H                                         H       H                                                                                      ##STR275##      CH.sub.3                                                                            H                                         F       H                                                                                      ##STR276##      CH.sub.3                                                                            H                                         H       CH.sub.3                                                                               ##STR277##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR278##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR279##      CH.sub.3                                                                            CH.sub.3                                  F       H                                                                                      ##STR280##      CH.sub.3                                                                            CH.sub.3                                  H       CH.sub.3                                                                               ##STR281##      CH.sub.3                                                                            CH.sub.3                                  F       CH.sub.3                                                                               ##STR282##      CH.sub.3                                                                            CH.sub.3                                  H       H                                                                                      ##STR283##      H    H                                         F       H                                                                                      ##STR284##      H    H                                         H       CH.sub.3                                                                               ##STR285##      H    H                                         F       CH.sub.3                                                                               ##STR286##      H    H                                         H       H                                                                                      ##STR287##      CH.sub.3                                                                            H                                         F       H                                                                                      ##STR288##      CH.sub.3                                                                            H                                         H       CH.sub.3                                                                               ##STR289##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR290##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR291##      CH.sub.3                                                                            CH.sub.3                                  F       H                                                                                      ##STR292##      CH.sub.3                                                                            CH.sub.3                                  H       CH.sub.3                                                                               ##STR293##      CH.sub.3                                                                            CH.sub.3                                  F       CH.sub.3                                                                               ##STR294##      CH.sub.3                                                                            CH.sub.3                                  H       H                                                                                      ##STR295##      CH.sub.3                                                                            CH.sub.3                                  F       H                                                                                      ##STR296##      CH.sub.3                                                                            CH.sub.3                                  H       CH.sub.3                                                                               ##STR297##      CH.sub.3                                                                            CH.sub.3                                  F       CH.sub.3                                                                               ##STR298##      CH.sub.3                                                                            CH.sub.3                                  H       H                                                                                      ##STR299##      H    H                                         F       H                                                                                      ##STR300##      H    H                                         H       CH.sub.3                                                                               ##STR301##      H    H                                         F       CH.sub.3                                                                               ##STR302##      H    H                                         H       H                                                                                      ##STR303##      CH.sub.3                                                                            H                                         F       H                                                                                      ##STR304##      CH.sub.3                                                                            H                                         H       CH.sub.3                                                                               ##STR305##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR306##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR307##      CH.sub.3                                                                            CH.sub.3                                  F       H                                                                                      ##STR308##      CH.sub.3                                                                            CH.sub.3                                  H       CH.sub.3                                                                               ##STR309##      CH.sub.3                                                                            CH.sub.3                                  F       CH.sub.3                                                                               ##STR310##      CH.sub.3                                                                            CH.sub.3                                  H       H                                                                                      ##STR311##      H    H                                         F       H                                                                                      ##STR312##      H    H                                         H       CH.sub.3                                                                               ##STR313##      H    H                                         F       CH.sub.3                                                                               ##STR314##      H    H                                         H       H                                                                                      ##STR315##      CH.sub.3                                                                            H                                         F       H                                                                                      ##STR316##      CH.sub.3                                                                            H                                         H       CH.sub.3                                                                               ##STR317##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR318##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR319##      H    H                                         F       H                                                                                      ##STR320##      H    H                                         H       CH.sub.3                                                                               ##STR321##      H    H                                         F       CH.sub.3                                                                               ##STR322##      H    H                                         H       H                                                                                      ##STR323##      H    H                                         F       H                                                                                      ##STR324##      H    H                                         H       CH.sub.3                                                                               ##STR325##      H    H                                         F       CH.sub.3                                                                               ##STR326##      H    H                                         H       H                                                                                      ##STR327##      H    H                                         F       H                                                                                      ##STR328##      H    H                                         H       CH.sub.3                                                                               ##STR329##      H    H                                         F       CH.sub.3                                                                               ##STR330##      H    H                                         H       H                                                                                      ##STR331##      H    H                                         F       H                                                                                      ##STR332##      H    H                                         H       CH.sub.3                                                                               ##STR333##      H    H                                         F       CH.sub.3                                                                               ##STR334##      H    H                                         H       H                                                                                      ##STR335##      H    H                                         F       H                                                                                      ##STR336##      H    H                                         H       CH.sub.3                                                                               ##STR337##      H    H                                         F       CH.sub.3                                                                               ##STR338##      H    H                                         H       H                                                                                      ##STR339##      CH.sub.3                                                                            H                                         F       H                                                                                      ##STR340##      CH.sub.3                                                                            H                                         H       CH.sub.3                                                                               ##STR341##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR342##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR343##      CH.sub.3                                                                            CH.sub.3                                  F       H                                                                                      ##STR344##      CH.sub.3                                                                            CH.sub.3                                  H       CH.sub.3                                                                               ##STR345##      CH.sub.3                                                                            CH.sub.3                                  F       CH.sub.3                                                                               ##STR346##      CH.sub.3                                                                            CH.sub.3                                  H       H                                                                                      ##STR347##      H    H                                         F       H                                                                                      ##STR348##      H    H                                         H       CH.sub.3                                                                               ##STR349##      H    H                                         F       CH.sub.3                                                                               ##STR350##      H    H                                         H       H                                                                                      ##STR351##      CH.sub.3                                                                            H                                         F       H                                                                                      ##STR352##      CH.sub.3                                                                            H                                         H       CH.sub.3                                                                               ##STR353##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR354##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR355##      CH.sub.3                                                                            CH.sub.3                                  F       H                                                                                      ##STR356##      CH.sub.3                                                                            CH.sub.3                                  H       CH.sub.3                                                                               ##STR357##      CH.sub.3                                                                            CH.sub.3                                  F       CH.sub.3                                                                               ##STR358##      CH.sub.3                                                                            CH.sub.3                                  H       H                                                                                      ##STR359##      H    H                                         F       H                                                                                      ##STR360##      H    H                                         H       CH.sub.3                                                                               ##STR361##      H    H                                         F       CH.sub.3                                                                               ##STR362##      H    H                                         H       H                                                                                      ##STR363##      CH.sub.3                                                                            H                                         F       H                                                                                      ##STR364##      CH.sub.3                                                                            H                                         H       CH.sub.3                                                                               ##STR365##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR366##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR367##      H    H                                         F       H                                                                                      ##STR368##      H    H                                         H       CH.sub.3                                                                               ##STR369##      H    H                                         F       CH.sub.3                                                                               ##STR370##      H    H                                         H       H                                                                                      ##STR371##      CH.sub.3                                                                            H                                         F       H                                                                                      ##STR372##      CH.sub. 3                                                                           H                                         H       CH.sub.3                                                                               ##STR373##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR374##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR375##      CH.sub.3                                                                            CH.sub.3                                  F       H                                                                                      ##STR376##      CH.sub.3                                                                            CH.sub.3                                  H       CH.sub.3                                                                               ##STR377##      CH.sub.3                                                                            CH.sub.3                                  F       CH.sub.3                                                                               ##STR378##      CH.sub.3                                                                            CH.sub.3                                  H       H                                                                                      ##STR379##      H    H                                         F       H                                                                                      ##STR380##      H    H                                         H       CH.sub.3                                                                               ##STR381##      H    H                                         F       CH.sub.3                                                                               ##STR382##      H    H                                         H       H                                                                                      ##STR383##      CH.sub.3                                                                            H                                         F       H                                                                                      ##STR384##      CH.sub.3                                                                            H                                         H       CH.sub.3                                                                               ##STR385##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR386##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR387##      CH.sub.3                                                                            CH.sub.3                                  F       H                                                                                      ##STR388##      CH.sub.3                                                                            CH.sub.3                                  H       CH.sub.3                                                                               ##STR389##      CH.sub.3                                                                            CH.sub.3                                  F       CH.sub.3                                                                               ##STR390##      CH.sub.3                                                                            CH.sub.3                                  H       H                                                                                      ##STR391##      CH.sub.3                                                                            CH.sub.3                                  F       H                                                                                      ##STR392##      CH.sub.3                                                                            CH.sub.3                                  H       CH.sub.3                                                                               ##STR393##      CH.sub.3                                                                            CH.sub.3                                  F       CH.sub.3                                                                               ##STR394##      CH.sub.3                                                                            CH.sub.3                                  H       H                                                                                      ##STR395##      H    H                                         F       H                                                                                      ##STR396##      H    H                                         H       CH.sub.3                                                                               ##STR397##      H    H                                         F       CH.sub.3                                                                               ##STR398##      H    H                                         H       H                                                                                      ##STR399##      CH.sub.3                                                                            H                                         F       H                                                                                      ##STR400##      CH.sub.3                                                                            H                                         H       CH.sub.3                                                                               ##STR401##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR402##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR403##      CH.sub.3                                                                            CH.sub.3                                  F       H                                                                                      ##STR404##      CH.sub.3                                                                            CH.sub.3                                  H       CH.sub.3                                                                               ##STR405##      CH.sub.3                                                                            CH.sub.3                                  F       CH.sub.3                                                                               ##STR406##      CH.sub.3                                                                            CH.sub.3                                  H       H                                                                                      ##STR407##      H    H                                         F       H                                                                                      ##STR408##      H    H                                         H       CH.sub.3                                                                               ##STR409##      H    H                                         F       CH.sub.3                                                                               ##STR410##      H    H                                         H       H                                                                                      ##STR411##      CH.sub.3                                                                            H                                         F       H                                                                                      ##STR412##      CH.sub.3                                                                            H                                         H       CH.sub.3                                                                               ##STR413##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR414##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR415##      H    H                                         F       H                                                                                      ##STR416##      H    H                                         H       CH.sub.3                                                                               ##STR417##      H    H                                         F       CH.sub.3                                                                               ##STR418##      H    H                                         H       H                                                                                      ##STR419##      CH.sub.3                                                                            H                                         F       H                                                                                      ##STR420##      CH.sub.3                                                                            H                                         H       CH.sub.3                                                                               ##STR421##      CH.sub.3                                                                            H                                         F       CH.sub.3                                                                               ##STR422##      CH.sub.3                                                                            H                                         H       H                                                                                      ##STR423##      CH.sub.3                                                                            CH.sub.3                                  F       H                                                                                      ##STR424##      CH.sub.3                                                                            CH.sub.3                                  H       CH.sub.3                                                                               ##STR425##      CH.sub.3                                                                            CH.sub.3                                  F       CH.sub.3                                                                               ##STR426##      CH.sub.3                                                                            CH.sub.3                                  H       H                                                                                      ##STR427##      H    H                                         F       H                                                                                      ##STR428##      H    H                                         H       CH.sub.3                                                                               ##STR429##      H    H                                         F       CH.sub.3                                                                               ##STR430##      H    H                                         H       H                                                                                      ##STR431##      H    H                                         F       H                                                                                      ##STR432##      H    H                                         H       CH.sub.3                                                                               ##STR433##      H    H                                         F       CH.sub.3                                                                               ##STR434##      H    H                                         H       H                                                                                      ##STR435##      H    H                                         F       H                                                                                      ##STR436##      H    H                                         H       CH.sub.3                                                                               ##STR437##      H    H                                         F       CH.sub.3                                                                               ##STR438##      H    H                                         ______________________________________                                    

                  TABLE IIa                                                        ______________________________________                                          ##STR439##                                                                    R.sup.1  R.sup.4  R.sup.5   A                                                  ______________________________________                                         H        H        H         H                                                  F        H        H         H                                                  H        CH.sub.3 H         H                                                  F        CH.sub.3 H         H                                                  H        H        H         CH.sub.3                                           F        H        H         CH.sub.3                                           H        CH.sub.3 H         CH.sub.3                                           F        CH.sub.3 H         CH.sub.3                                           H        H        H         CH.sub.2 CH.sub.3                                  F        H        H         CH.sub.2 CH.sub.3                                  H        CH.sub.3 H         CH.sub.2 CH.sub.3                                  F        CH.sub.3 H         CH.sub.2 CH.sub.3                                  H        H        H         CH(CH.sub.3).sub.2                                 F        H        H         CH(CH.sub.3).sub.2                                 H        CH.sub.3 H         CH(CH.sub.3).sub.2                                 F        CH.sub.3 H         CH(CH.sub.3).sub.2                                 H        H        H         CH.sub.2 CHCH.sub.2                                F        H        H         CH.sub.2 CHCH.sub.2                                H        CH.sub. 3                                                                               H         CH.sub.2 CHCH.sub.2                                F        CH.sub.3 H         CH.sub.2 CHCH.sub.2                                H        H        H         CH.sub.2 CHCHCH.sub.3                              F        H        H         CH.sub.2 CHCHCH.sub.3                              H        CH.sub.3 H         CH.sub.2 CHCHCH.sub.3                              F        CH.sub.3 H         CH.sub.2 CHCHCH.sub.3                              H        H        H         CH.sub.2 CCH                                       F        H        H         CH.sub.2 CCH                                       H        CH.sub.3 H         CH.sub.2 CCH                                       F        CH.sub.3 H         CH.sub.2 CCH                                       H        H        H         CH.sub.2 CCCH.sub.3                                F        H        H         CH.sub.2 CCCH.sub.3                                H        CH.sub.3 H         CH.sub.2 CCCH.sub.3                                F        CH.sub.3 H         CH.sub.2 CCCH.sub.3                                H        H        H         CH.sub.2 OCH.sub.3                                 F        H        H         CH.sub.2 OCH.sub.3                                 H        CH.sub.3 H         CH.sub.2 OCH.sub.3                                 F        CH.sub.3 H         CH.sub.2 OCH.sub.3                                 H        H        H         (CH.sub.2).sub.2 OCH.sub.3                         F        H        H         (CH.sub.2).sub.2 OCH.sub.3                         H        CH.sub.3 H         (CH.sub.2).sub.2 OCH.sub.3                         F        CH.sub.3 H         (CH.sub.2).sub.2 OCH.sub.3                         H        H        H         CH.sub.2 CO.sub.2 CH.sub.3                         F        H        H         CH.sub.2 CO.sub.2 CH.sub.3                         H        CH.sub.3 H         CH.sub.2 CO.sub.2 CH.sub.3                         F        CH.sub.3 H         CH.sub.2 CO.sub.2 CH.sub.3                         H        H        H         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                F        H        H         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                H        CH.sub.3 H         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                F        CH.sub.3 H         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                H        H        H         CH(CH.sub.3)CO.sub.2 CH.sub.3                      F        H        H         CH(CH.sub.3)CO.sub.2 CH.sub.3                      H        CH.sub.3 H         CH(CH.sub.3)CO.sub.2 CH.sub.3                      F        CH.sub.3 H         CH(CH.sub.3)CO.sub.2 CH.sub.3                      H        H        H         CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3             F        H        H         CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3             H        CH.sub. 3                                                                               H         CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3             F        CH.sub.3 H         CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3             H        CH.sub.3 CH.sub.3  H                                                  F        CH.sub.3 CH.sub.3  H                                                  H        CH.sub.3 CH.sub.3  CH.sub.3                                           F        CH.sub.3 CH.sub.3  CH.sub.3                                           H        CH.sub.3 CH.sub.3  CH.sub.2 CH.sub.3                                  F        CH.sub.3 CH.sub.3  CH.sub.2 CH.sub.3                                  H        CH.sub.3 CH.sub.3  CH.sub.2 CHCH.sub.2                                F        CH.sub.3 CH.sub.3  CH.sub.2 CHCH.sub.2                                H        CH.sub.3 CH.sub.3  CH.sub.2 CCH                                       F        CH.sub.3 CH.sub.3  CH.sub.2 CCH                                       H        CH.sub.3 CH.sub.3  (CH.sub.2).sub.2 OCH.sub.3                         F        CH.sub.3 CH.sub.3  (CH.sub.2).sub.2 OCH.sub.3                         H        CH.sub.3 CH.sub.3  CH.sub.2 CO.sub.2 CH.sub.3                         F        CH.sub.3 CH.sub.3  CH.sub.2 CO.sub.2 CH.sub.3                         H        CH.sub.3 CH.sub.3  CH(CH.sub.3)CO.sub.2 CH.sub.3                      F        CH.sub.3 CH.sub.3  CH(CH.sub.3)CO.sub.2 CH.sub.3                      ______________________________________                                    

                  TABLE III                                                        ______________________________________                                          ##STR440##                                                                    R.sup.1                                                                               R.sup.2  R.sup.3        R.sup.4                                                                               R.sup.5                                  ______________________________________                                         H      H                                                                                        ##STR441##    H      H                                        F      H                                                                                        ##STR442##    H      H                                        H      CH.sub.3                                                                                 ##STR443##    H      H                                        F      CH.sub.3                                                                                 ##STR444##    H      H                                        H      H                                                                                        ##STR445##    H      H                                        F      H                                                                                        ##STR446##    H      H                                        H      CH.sub.3                                                                                 ##STR447##    H      H                                        F      CH.sub.3                                                                                 ##STR448##    H      H                                        H      H                                                                                        ##STR449##    H      H                                        F      H                                                                                        ##STR450##    H      H                                        H      CH.sub.3                                                                                 ##STR451##    H      H                                        F      CH.sub.3                                                                                 ##STR452##    H      H                                        H      H                                                                                        ##STR453##    H      H                                        F      H                                                                                        ##STR454##    H      H                                        H      CH.sub.3                                                                                 ##STR455##    H      H                                        F      CH.sub.3                                                                                 ##STR456##    H      H                                        H      H                                                                                        ##STR457##    H      H                                        F      H                                                                                        ##STR458##    H      H                                        H      CH.sub.3                                                                                 ##STR459##    H      H                                        F      CH.sub.3                                                                                 ##STR460##    H      H                                        H      H                                                                                        ##STR461##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR462##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR463##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR464##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR465##    CH.sub.3                                                                              CH.sub.3                                 F      H                                                                                        ##STR466##    CH.sub.3                                                                              CH.sub.3                                 H      CH.sub.3                                                                                 ##STR467##    CH.sub.3                                                                              CH.sub.3                                 F      CH.sub.3                                                                                 ##STR468##    CH.sub.3                                                                              CH.sub.3                                 H      H                                                                                        ##STR469##    H      H                                        F      H                                                                                        ##STR470##    H      H                                        H      CH.sub.3                                                                                 ##STR471##    H      H                                        F      CH.sub.3                                                                                 ##STR472##    H      H                                        H      H                                                                                        ##STR473##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR474##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR475##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR476##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR477##    CH.sub.3                                                                              CH.sub.3                                 F      H                                                                                        ##STR478##    CH.sub.3                                                                              CH.sub.3                                 H      CH.sub.3                                                                                 ##STR479##    CH.sub.3                                                                              CH.sub.3                                 F      CH.sub.3                                                                                 ##STR480##    CH.sub.3                                                                              CH.sub.3                                 H      H                                                                                        ##STR481##    H      H                                        F      H                                                                                        ##STR482##    H      H                                        H      CH.sub.3                                                                                 ##STR483##    H      H                                        F      CH.sub.3                                                                                 ##STR484##    H      H                                        H      H                                                                                        ##STR485##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR486##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR487##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR488##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR489##    H      H                                        F      H                                                                                        ##STR490##    H      H                                        H      CH.sub.3                                                                                 ##STR491##    H      H                                        F      CH.sub.3                                                                                 ##STR492##    H      H                                        H      H                                                                                        ##STR493##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR494##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR495##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR496##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR497##    CH.sub.3                                                                              CH.sub.3                                 F      H                                                                                        ##STR498##    CH.sub.3                                                                              CH.sub.3                                 H      CH.sub.3                                                                                 ##STR499##    CH.sub.3                                                                              CH.sub.3                                 F      CH.sub.3                                                                                 ##STR500##    CH.sub.3                                                                              CH.sub.3                                 H      H                                                                                        ##STR501##    H      H                                        F      H                                                                                        ##STR502##    H      H                                        H      CH.sub.3                                                                                 ##STR503##    H      H                                        F      CH.sub.3                                                                                 ##STR504##    H      H                                        H      H                                                                                        ##STR505##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR506##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR507##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR508##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR509##    CH.sub.3                                                                              CH.sub.3                                 F      H                                                                                        ##STR510##    CH.sub.3                                                                              CH.sub.3                                 H      CH.sub.3                                                                                 ##STR511##    CH.sub.3                                                                              CH.sub.3                                 F      CH.sub.3                                                                                 ##STR512##    CH.sub.3                                                                              CH.sub.3                                 H      H                                                                                        ##STR513##    CH.sub.3                                                                              CH.sub.3                                 F      H                                                                                        ##STR514##    CH.sub.3                                                                              CH.sub.3                                 H      CH.sub.3                                                                                 ##STR515##    CH.sub.3                                                                              CH.sub.3                                 F      CH.sub.3                                                                                 ##STR516##    CH.sub.3                                                                              CH.sub.3                                 H      H                                                                                        ##STR517##    H      H                                        F      H                                                                                        ##STR518##    H      H                                        H      CH.sub.3                                                                                 ##STR519##    H      H                                        F      CH.sub.3                                                                                 ##STR520##    H      H                                        H      H                                                                                        ##STR521##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR522##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR523##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR524##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR525##    CH.sub.3                                                                              CH.sub.3                                 F      H                                                                                        ##STR526##    CH.sub.3                                                                              CH.sub.3                                 H      CH.sub.3                                                                                 ##STR527##    CH.sub.3                                                                              CH.sub.3                                 F      CH.sub.3                                                                                 ##STR528##    CH.sub.3                                                                              CH.sub.3                                 H      H                                                                                        ##STR529##    H      H                                        F      H                                                                                        ##STR530##    H      H                                        H      CH.sub.3                                                                                 ##STR531##    H      H                                        F      CH.sub.3                                                                                 ##STR532##    H      H                                        H      H                                                                                        ##STR533##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR534##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR535##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR536##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR537##    H      H                                        F      H                                                                                        ##STR538##    H      H                                        H      CH.sub.3                                                                                 ##STR539##    H      H                                        F      CH.sub.3                                                                                 ##STR540##    H      H                                        H      H                                                                                        ##STR541##    H      H                                        F      H                                                                                        ##STR542##    H      H                                        H      CH.sub.3                                                                                 ##STR543##    H      H                                        F      CH.sub.3                                                                                 ##STR544##    H      H                                        H      H                                                                                        ##STR545##    H      H                                        F      H                                                                                        ##STR546##    H      H                                        H      CH.sub.3                                                                                 ##STR547##    H      H                                        F      CH.sub.3                                                                                 ##STR548##    H      H                                        H      H                                                                                        ##STR549##    H      H                                        F      H                                                                                        ##STR550##    H      H                                        H      CH.sub.3                                                                                 ##STR551##    H      H                                        F      CH.sub.3                                                                                 ##STR552##    H      H                                        H      H                                                                                        ##STR553##    H      H                                        F      H                                                                                        ##STR554##    H      H                                        H      CH.sub.3                                                                                 ##STR555##    H      H                                        F      CH.sub.3                                                                                 ##STR556##    H      H                                        H      H                                                                                        ##STR557##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR558##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR559##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR560##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR561##    CH.sub.3                                                                              CH.sub.3                                 F      H                                                                                        ##STR562##    CH.sub.3                                                                              CH.sub.3                                 H      CH.sub.3                                                                                 ##STR563##    CH.sub.3                                                                              CH.sub.3                                 F      CH.sub.3                                                                                 ##STR564##    CH.sub.3                                                                              CH.sub.3                                 H      H                                                                                        ##STR565##    H      H                                        F      H                                                                                        ##STR566##    H      H                                        H      CH.sub.3                                                                                 ##STR567##    H      H                                        F      CH.sub.3                                                                                 ##STR568##    H      H                                        H      H                                                                                        ##STR569##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR570##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR571##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR572##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR573##    CH.sub.3                                                                              CH.sub.3                                 F      H                                                                                        ##STR574##    CH.sub.3                                                                              CH.sub.3                                 H      CH.sub.3                                                                                 ##STR575##    CH.sub.3                                                                              CH.sub.3                                 F      CH.sub.3                                                                                 ##STR576##    CH.sub.3                                                                              CH.sub.3                                 H      H                                                                                        ##STR577##    H      H                                        F      H                                                                                        ##STR578##    H      H                                        H      CH.sub.3                                                                                 ##STR579##    H      H                                        F      CH.sub.3                                                                                 ##STR580##    H      H                                        H      H                                                                                        ##STR581##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR582##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR583##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR584##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR585##    H      H                                        F      H                                                                                        ##STR586##    H      H                                        F      CH.sub.3                                                                                 ##STR587##    H      H                                        F      CH.sub.3                                                                                 ##STR588##    H      H                                        H      H                                                                                        ##STR589##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR590##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR591##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR592##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR593##    CH.sub.3                                                                              CH.sub.3                                 F      H                                                                                        ##STR594##    CH.sub.3                                                                              CH.sub.3                                 H      CH.sub.3                                                                                 ##STR595##    CH.sub.3                                                                              CH.sub.3                                 F      CH.sub.3                                                                                 ##STR596##    CH.sub.3                                                                              CH.sub.3                                 H      H                                                                                        ##STR597##    H      H                                        F      H                                                                                        ##STR598##    H      H                                        H      CH.sub.3                                                                                 ##STR599##    H      H                                        F      CH.sub.3                                                                                 ##STR600##    H      H                                        H      H                                                                                        ##STR601##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR602##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR603##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR604##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR605##    CH.sub.3                                                                              CH.sub.3                                 F      H                                                                                        ##STR606##    CH.sub.3                                                                              CH.sub.3                                 H      CH.sub.3                                                                                 ##STR607##    CH.sub.3                                                                              CH.sub.3                                 F      CH.sub.3                                                                                 ##STR608##    CH.sub.3                                                                              CH.sub.3                                 H      H                                                                                        ##STR609##    CH.sub.3                                                                              CH.sub.3                                 F      H                                                                                        ##STR610##    CH.sub.3                                                                              CH.sub.3                                 H      CH.sub.3                                                                                 ##STR611##    CH.sub.3                                                                              CH.sub.3                                 F      CH.sub.3                                                                                 ##STR612##    CH.sub.3                                                                              CH.sub.3                                 H      H                                                                                        ##STR613##    H      H                                        F      H                                                                                        ##STR614##    H      H                                        H      CH.sub.3                                                                                 ##STR615##    H      H                                        F      CH.sub.3                                                                                 ##STR616##    H      H                                        H      H                                                                                        ##STR617##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR618##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR619##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR620##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR621##    CH.sub.3                                                                              CH.sub.3                                 F      H                                                                                        ##STR622##    CH.sub.3                                                                              CH.sub.3                                 H      CH.sub.3                                                                                 ##STR623##    CH.sub.3                                                                              CH.sub.3                                 F      CH.sub.3                                                                                 ##STR624##    CH.sub.3                                                                              CH.sub.3                                 H      H                                                                                        ##STR625##    H      H                                        F      H                                                                                        ##STR626##    H      H                                        H      CH.sub.3                                                                                 ##STR627##    H      H                                        F      CH.sub.3                                                                                 ##STR628##    H      H                                        H      H                                                                                        ##STR629##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR630##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR631##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR632##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR633##    H      H                                        F      H                                                                                        ##STR634##    H      H                                        H      CH.sub.3                                                                                 ##STR635##    H      H                                        F      CH.sub.3                                                                                 ##STR636##    H      H                                        H      H                                                                                        ##STR637##    CH.sub.3                                                                              H                                        F      H                                                                                        ##STR638##    CH.sub.3                                                                              H                                        H      CH.sub.3                                                                                 ##STR639##    CH.sub.3                                                                              H                                        F      CH.sub.3                                                                                 ##STR640##    CH.sub.3                                                                              H                                        H      H                                                                                        ##STR641##    CH.sub.3                                                                              CH.sub.3                                 F      H                                                                                        ##STR642##    CH.sub.3                                                                              CH.sub.3                                 H      CH.sub.3                                                                                 ##STR643##    CH.sub.3                                                                              CH.sub.3                                 F      CH.sub.3                                                                                 ##STR644##    CH.sub.3                                                                              CH.sub.3                                 H      H                                                                                        ##STR645##    H      H                                        F      H                                                                                        ##STR646##    H      H                                        H      CH.sub.3                                                                                 ##STR647##    H      H                                        F      CH.sub.3                                                                                 ##STR648##    H      H                                        H      H                                                                                        ##STR649##    H      H                                        F      H                                                                                        ##STR650##    H      H                                        H      CH.sub.3                                                                                 ##STR651##    H      H                                        F      CH.sub.3                                                                                 ##STR652##    H      H                                        H      H                                                                                        ##STR653##    H      H                                        F      H                                                                                        ##STR654##    H      H                                        H      CH.sub.3                                                                                 ##STR655##    H      H                                        F      CH.sub.3                                                                                 ##STR656##    H      H                                        ______________________________________                                    

                  TABLE IIIa                                                       ______________________________________                                          ##STR657##                                                                    R.sup.1  R.sup.4  R.sup.5   A                                                  ______________________________________                                         H        H        H         H                                                  F        H        H         H                                                  H        CH.sub.3 H         H                                                  F        CH.sub.3 H         H                                                  H        H        H         CH.sub.3                                           F        H        H         CH.sub.3                                           H        CH.sub.3 H         CH.sub.3                                           F        CH.sub.3 H         CH.sub.3                                           H        H        H         CH.sub.2 CH.sub.3                                  F        H        H         CH.sub.2 CH.sub.3                                  H        CH.sub.3 H         CH.sub.2 CH.sub.3                                  F        CH.sub.3 H         CH.sub.2 CH.sub.3                                  H        H        H         CH(CH.sub.3).sub.2                                 F        H        H         CH(CH.sub.3).sub.2                                 H        CH.sub.3 H         CH(CH.sub.3).sub.2                                 F        CH.sub.3 H         CH(CH.sub.3).sub.2                                 H        H        H         CH.sub.2 CHCH.sub.2                                F        H        H         CH.sub.2 CHCH.sub.2                                H        CH.sub.3 H         CH.sub.2 CHCH.sub.2                                F        CH.sub.3 H         CH.sub.2 CHCH.sub.2                                H        H        H         CH.sub.2 CHCHCH.sub.3                              F        H        H         CH.sub.2 CHCHCH.sub.3                              H        CH.sub.3 H         CH.sub.2 CHCHCH.sub.3                              F        CH.sub.3 H         CH.sub.2 CHCHCH.sub.3                              H        H        H         CH.sub.2 CCH                                       F        H        H         CH.sub.2 CCH                                       H        CH.sub.3 H         CH.sub.2 CCH                                       F        CH.sub.3 H         CH.sub.2 CCH                                       H        H        H         CH.sub.2 CCCH.sub.3                                F        H        H         CH.sub.2 CCCH.sub.3                                H        CH.sub.3 H         CH.sub.2 CCCH.sub.3                                F        CH.sub.3 H         CH.sub.2 CCCH.sub.3                                H        H        H         CH.sub.2 OCH.sub.3                                 F        H        H         CH.sub.2 OCH.sub.3                                 H        CH.sub.3 H         CH.sub.2 OCH.sub. 3                                F        CH.sub.3 H         CH.sub.2 OCH.sub.3                                 H        H        H         (CH.sub.2).sub.2 OCH.sub.3                         F        H        H         (CH.sub.2).sub.2 OCH.sub.3                         H        CH.sub.3 H         (CH.sub.2).sub.2 OCH.sub.3                         F        CH.sub.3 H         (CH.sub.2).sub.2 OCH.sub.3                         H        H        H         CH.sub.2 CO.sub.2 CH.sub.3                         F        H        H         CH.sub.2 CO.sub.2 CH.sub.3                         H        CH.sub.3 H         CH.sub.2 CO.sub.2 CH.sub.3                         F        CH.sub.3 H         CH.sub.2 CO.sub.2 CH.sub.3                         H        H        H         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                F        H        H         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                H        CH.sub.3 H         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                F        CH.sub.3 H         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                H        H        H         CH(CH.sub.3)CO.sub.2 CH.sub.3                      F        H        H         CH(CH.sub.3)CO.sub.2 CH.sub.3                      H        CH.sub.3 H         CH(CH.sub.3)CO.sub.2 CH.sub.3                      F        CH.sub.3 H         CH(CH.sub.3)CO.sub.2 CH.sub.3                      H        H        H         CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3             F        H        H         CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3             H        CH.sub.3 H         CH(CH.sub.3)CO.sub.2 CH.sub. 2 CH.sub.3            F        CH.sub.3 H         CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3             H        CH.sub.3 CH.sub.3  H                                                  F        CH.sub.3 CH.sub.3  H                                                  H        CH.sub.3 CH.sub.3  CH.sub.3                                           F        CH.sub.3 CH.sub.3  CH.sub.3                                           H        CH.sub.3 CH.sub.3  CH.sub.2 CH.sub.3                                  F        CH.sub.3 CH.sub.3  CH.sub.2 CH.sub.3                                  H        CH.sub.3 CH.sub.3  CH.sub.2 CHCH.sub.2                                F        CH.sub.3 CH.sub.3  CH.sub.2 CHCH.sub.2                                H        CH.sub.3 CH.sub.3  CH.sub.2 CCH                                       F        CH.sub.3 CH.sub.3  CH.sub.2 CCH                                       H        CH.sub.3 CH.sub.3  (CH.sub.2).sub.2 OCH.sub.3                         F        CH.sub.3 CH.sub.3  (CH.sub.2).sub.2 OCH.sub.3                         H        CH.sub.3 CH.sub.3  CH.sub.2 CO.sub.2 CH.sub.3                         F        CH.sub.3 CH.sub.3  CH.sub.2 CO.sub.2 CH.sub.3                         H        CH.sub.3 CH.sub.3  CH(CH.sub.3)CO.sub.2 CH.sub.3                      F        CH.sub.3 CH.sub.3  CH(CH.sub.3)CO.sub.2 CH.sub.3                      ______________________________________                                    

                  TABLE IV                                                         ______________________________________                                          ##STR658##                                                                    R.sup.1     R.sup.2                                                                               R.sup.3                                                     ______________________________________                                         H           H                                                                                      ##STR659##                                                 F           H                                                                                      ##STR660##                                                 H           CH.sub.3                                                                               ##STR661##                                                 F           CH.sub.3                                                                               ##STR662##                                                 H           H                                                                                      ##STR663##                                                 F           H                                                                                      ##STR664##                                                 H           CH.sub.3                                                                               ##STR665##                                                 F           CH.sub.3                                                                               ##STR666##                                                 H           H                                                                                      ##STR667##                                                 F           H                                                                                      ##STR668##                                                 H           CH.sub.3                                                                               ##STR669##                                                 F           CH.sub.3                                                                               ##STR670##                                                 H           H                                                                                      ##STR671##                                                 F           H                                                                                      ##STR672##                                                 H           CH.sub.3                                                                               ##STR673##                                                 F           CH.sub.3                                                                               ##STR674##                                                 H           H                                                                                      ##STR675##                                                 F           H                                                                                      ##STR676##                                                 H           CH.sub.3                                                                               ##STR677##                                                 F           CH.sub.3                                                                               ##STR678##                                                 H           H                                                                                      ##STR679##                                                 F           H                                                                                      ##STR680##                                                 H           CH.sub.3                                                                               ##STR681##                                                 F           CH.sub.3                                                                               ##STR682##                                                 H           H                                                                                      ##STR683##                                                 F           H                                                                                      ##STR684##                                                 H           CH.sub.3                                                                               ##STR685##                                                 F           CH.sub.3                                                                               ##STR686##                                                 H           H                                                                                      ##STR687##                                                 F           H                                                                                      ##STR688##                                                 H           CH.sub.3                                                                               ##STR689##                                                 F           CH.sub.3                                                                               ##STR690##                                                 H           H                                                                                      ##STR691##                                                 F           H                                                                                      ##STR692##                                                 H           CH.sub.3                                                                               ##STR693##                                                 F           CH.sub.3                                                                               ##STR694##                                                 H           H                                                                                      ##STR695##                                                 F           H                                                                                      ##STR696##                                                 H           CH.sub.3                                                                               ##STR697##                                                 F           CH.sub.3                                                                               ##STR698##                                                 H           H                                                                                      ##STR699##                                                 F           H                                                                                      ##STR700##                                                 H           CH.sub.3                                                                               ##STR701##                                                 F           CH.sub.3                                                                               ##STR702##                                                 H           H                                                                                      ##STR703##                                                 F           H                                                                                      ##STR704##                                                 H           CH.sub.3                                                                               ##STR705##                                                 F           CH.sub.3                                                                               ##STR706##                                                 H           H                                                                                      ##STR707##                                                 F           H                                                                                      ##STR708##                                                 H           CH.sub.3                                                                               ##STR709##                                                 F           CH.sub.3                                                                               ##STR710##                                                 H           H                                                                                      ##STR711##                                                 F           H                                                                                      ##STR712##                                                 H           CH.sub.3                                                                               ##STR713##                                                 F           CH.sub.3                                                                               ##STR714##                                                 H           H                                                                                      ##STR715##                                                 F           H                                                                                      ##STR716##                                                 H           CH.sub.3                                                                               ##STR717##                                                 F           CH.sub.3                                                                               ##STR718##                                                 H           H                                                                                      ##STR719##                                                 F           H                                                                                      ##STR720##                                                 H           CH.sub.3                                                                               ##STR721##                                                 F           CH.sub.3                                                                               ##STR722##                                                 H           H                                                                                      ##STR723##                                                 F           H                                                                                      ##STR724##                                                 H           CH.sub.3                                                                               ##STR725##                                                 F           CH.sub.3                                                                               ##STR726##                                                 H           H                                                                                      ##STR727##                                                 F           H                                                                                      ##STR728##                                                 H           CH.sub.3                                                                               ##STR729##                                                 F           CH.sub.3                                                                               ##STR730##                                                 H           H                                                                                      ##STR731##                                                 F           H                                                                                      ##STR732##                                                 H           CH.sub.3                                                                               ##STR733##                                                 F           CH.sub.3                                                                               ##STR734##                                                 H           H                                                                                      ##STR735##                                                 F           H                                                                                      ##STR736##                                                 H           CH.sub.3                                                                               ##STR737##                                                 F           CH.sub.3                                                                               ##STR738##                                                 H           H                                                                                      ##STR739##                                                 F           H                                                                                      ##STR740##                                                 H           CH.sub.3                                                                               ##STR741##                                                 F           CH.sub.3                                                                               ##STR742##                                                 H           H                                                                                      ##STR743##                                                 F           H                                                                                      ##STR744##                                                 H           CH.sub.3                                                                               ##STR745##                                                 F           CH.sub.3                                                                               ##STR746##                                                 H           H                                                                                      ##STR747##                                                 F           H                                                                                      ##STR748##                                                 H           CH.sub.3                                                                               ##STR749##                                                 F           CH.sub.3                                                                               ##STR750##                                                 H           H                                                                                      ##STR751##                                                 F           H                                                                                      ##STR752##                                                 H           CH.sub.3                                                                               ##STR753##                                                 F           CH.sub.3                                                                               ##STR754##                                                 H           H                                                                                      ##STR755##                                                 F           H                                                                                      ##STR756##                                                 H           CH.sub. 3                                                                              ##STR757##                                                 F           CH.sub.3                                                                               ##STR758##                                                 H           H                                                                                      ##STR759##                                                 F           H                                                                                      ##STR760##                                                 H           CH.sub.3                                                                               ##STR761##                                                 F           CH.sub.3                                                                               ##STR762##                                                 ______________________________________                                    

                  TABLE IVa                                                        ______________________________________                                          ##STR763##                                                                    R.sup.1         A                                                              ______________________________________                                         H               H                                                              F               H                                                              H               CH.sub.3                                                       F               CH.sub.3                                                       H               CH.sub.2 CH.sub.3                                              F               CH.sub.2 CH.sub.3                                              H               CH(CH.sub.3).sub.2                                             F               CH(CH.sub.3).sub.2                                             H               CH.sub.2 CHCH.sub.2                                            F               CH.sub.2 CHCH.sub.2                                            H               CH.sub.2 CHCHCH.sub.3                                          F               CH.sub.2 CHCHCH.sub.3                                          H               CH.sub.2 CCH                                                   F               CH.sub.2 CCH                                                   H               CH.sub.2 CCCH.sub.3                                            F               CH.sub.2 CCCH.sub.3                                            H               CH.sub.2 OCH.sub.3                                             F               CH.sub.2 OCH.sub.3                                             H               (CH.sub.2).sub.2 OCH.sub.3                                     F               (CH.sub.2).sub.2 OCH.sub.3                                     H               CH.sub.2 CO.sub.2 CH.sub.3                                     F               CH.sub.2 CO.sub.2 CH.sub.3                                     H               CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                            F               CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                            H               CH(CH.sub.3)CO.sub.2 CH.sub.3                                  F               CH(CH.sub.3)CO.sub.2 CH.sub.3                                  H               CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                         F               CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                         ______________________________________                                    

                  TABLE V                                                          ______________________________________                                          ##STR764##                                                                    R.sup.1     R.sup.2                                                                               R.sup.3                                                     ______________________________________                                         H           H                                                                                      ##STR765##                                                 F           H                                                                                      ##STR766##                                                 H           CH.sub.3                                                                               ##STR767##                                                 F           CH.sub.3                                                                               ##STR768##                                                 H           H                                                                                      ##STR769##                                                 F           H                                                                                      ##STR770##                                                 H           CH.sub.3                                                                               ##STR771##                                                 F           CH.sub.3                                                                               ##STR772##                                                 H           H                                                                                      ##STR773##                                                 F           H                                                                                      ##STR774##                                                 H           CH.sub.3                                                                               ##STR775##                                                 F           CH.sub.3                                                                               ##STR776##                                                 H           H                                                                                      ##STR777##                                                 F           H                                                                                      ##STR778##                                                 H           CH.sub.3                                                                               ##STR779##                                                 F           CH.sub.3                                                                               ##STR780##                                                 H           H                                                                                      ##STR781##                                                 F           H                                                                                      ##STR782##                                                 H           CH.sub.3                                                                               ##STR783##                                                 F           CH.sub.3                                                                               ##STR784##                                                 H           H                                                                                      ##STR785##                                                 F           H                                                                                      ##STR786##                                                 H           CH.sub.3                                                                               ##STR787##                                                 F           CH.sub.3                                                                               ##STR788##                                                 H           H                                                                                      ##STR789##                                                 F           H                                                                                      ##STR790##                                                 H           CH.sub.3                                                                               ##STR791##                                                 F           CH.sub.3                                                                               ##STR792##                                                 H           H                                                                                      ##STR793##                                                 F           H                                                                                      ##STR794##                                                 H           CH.sub.3                                                                               ##STR795##                                                 F           CH.sub.3                                                                               ##STR796##                                                 H           H                                                                                      ##STR797##                                                 F           H                                                                                      ##STR798##                                                 H           CH.sub.3                                                                               ##STR799##                                                 F           CH.sub.3                                                                               ##STR800##                                                 H           H                                                                                      ##STR801##                                                 F           H                                                                                      ##STR802##                                                 H           CH.sub.3                                                                               ##STR803##                                                 F           CH.sub.3                                                                               ##STR804##                                                 H           H                                                                                      ##STR805##                                                 F           H                                                                                      ##STR806##                                                 H           CH.sub.3                                                                               ##STR807##                                                 F           CH.sub.3                                                                               ##STR808##                                                 H           H                                                                                      ##STR809##                                                 F           H                                                                                      ##STR810##                                                 H           CH.sub.3                                                                               ##STR811##                                                 F           CH.sub.3                                                                               ##STR812##                                                 H           H                                                                                      ##STR813##                                                 F           H                                                                                      ##STR814##                                                 H           CH.sub.3                                                                               ##STR815##                                                 F           CH.sub.3                                                                               ##STR816##                                                 H           H                                                                                      ##STR817##                                                 F           H                                                                                      ##STR818##                                                 H           CH.sub.3                                                                               ##STR819##                                                 F           CH.sub.3                                                                               ##STR820##                                                 H           H                                                                                      ##STR821##                                                 F           H                                                                                      ##STR822##                                                 H           CH.sub.3                                                                               ##STR823##                                                 F           CH.sub.3                                                                               ##STR824##                                                 H           H                                                                                      ##STR825##                                                 F           H                                                                                      ##STR826##                                                 H           CH.sub.3                                                                               ##STR827##                                                 F           CH.sub.3                                                                               ##STR828##                                                 H           H                                                                                      ##STR829##                                                 F           H                                                                                      ##STR830##                                                 H           CH.sub.3                                                                               ##STR831##                                                 F           CH.sub.3                                                                               ##STR832##                                                 H           H                                                                                      ##STR833##                                                 F           H                                                                                      ##STR834##                                                 H           CH.sub.3                                                                               ##STR835##                                                 F           CH.sub.3                                                                               ##STR836##                                                 H           H                                                                                      ##STR837##                                                 F           H                                                                                      ##STR838##                                                 H           CH.sub.3                                                                               ##STR839##                                                 F           CH.sub.3                                                                               ##STR840##                                                 H           H                                                                                      ##STR841##                                                 F           H                                                                                      ##STR842##                                                 H           CH.sub.3                                                                               ##STR843##                                                 F           CH.sub.3                                                                               ##STR844##                                                 H           H                                                                                      ##STR845##                                                 F           H                                                                                      ##STR846##                                                 H           CH.sub.3                                                                               ##STR847##                                                 F           CH.sub.3                                                                               ##STR848##                                                 H           H                                                                                      ##STR849##                                                 F           H                                                                                      ##STR850##                                                 H           CH.sub.3                                                                               ##STR851##                                                 F           CH.sub.3                                                                               ##STR852##                                                 H           H                                                                                      ##STR853##                                                 F           H                                                                                      ##STR854##                                                 H           CH.sub.3                                                                               ##STR855##                                                 F           CH.sub.3                                                                               ##STR856##                                                 H           H                                                                                      ##STR857##                                                 F           H                                                                                      ##STR858##                                                 H           CH.sub.3                                                                               ##STR859##                                                 F           CH.sub.3                                                                               ##STR860##                                                 H           H                                                                                      ##STR861##                                                 F           H                                                                                      ##STR862##                                                 H           CH.sub.3                                                                               ##STR863##                                                 F           CH.sub.3                                                                               ##STR864##                                                 H           H                                                                                      ##STR865##                                                 F           H                                                                                      ##STR866##                                                 H           CH.sub.3                                                                               ##STR867##                                                 F           CH.sub.3                                                                               ##STR868##                                                 ______________________________________                                    

                  TABLE VI                                                         ______________________________________                                          ##STR869##                                                                    R.sup.1     R.sup.2                                                                               R.sup.3                                                     ______________________________________                                         H           H                                                                                      ##STR870##                                                 F           H                                                                                      ##STR871##                                                 H           CH.sub.3                                                                               ##STR872##                                                 F           CH.sub.3                                                                               ##STR873##                                                 H           H                                                                                      ##STR874##                                                 F           H                                                                                      ##STR875##                                                 H           CH.sub.3                                                                               ##STR876##                                                 F           CH.sub.3                                                                               ##STR877##                                                 H           H                                                                                      ##STR878##                                                 F           H                                                                                      ##STR879##                                                 H           CH.sub.3                                                                               ##STR880##                                                 F           CH.sub.3                                                                               ##STR881##                                                 H           H                                                                                      ##STR882##                                                 F           H                                                                                      ##STR883##                                                 H           CH.sub.3                                                                               ##STR884##                                                 F           CH.sub.3                                                                               ##STR885##                                                 H           H                                                                                      ##STR886##                                                 F           H                                                                                      ##STR887##                                                 H           CH.sub.3                                                                               ##STR888##                                                 F           CH.sub.3                                                                               ##STR889##                                                 H           H                                                                                      ##STR890##                                                 F           H                                                                                      ##STR891##                                                 H           CH.sub.3                                                                               ##STR892##                                                 F           CH.sub.3                                                                               ##STR893##                                                 H           H                                                                                      ##STR894##                                                 F           H                                                                                      ##STR895##                                                 H           CH.sub.3                                                                               ##STR896##                                                 F           CH.sub.3                                                                               ##STR897##                                                 H           H                                                                                      ##STR898##                                                 F           H                                                                                      ##STR899##                                                 H           CH.sub.3                                                                               ##STR900##                                                 F           CH.sub.3                                                                               ##STR901##                                                 H           H                                                                                      ##STR902##                                                 F           H                                                                                      ##STR903##                                                 H           CH.sub.3                                                                               ##STR904##                                                 F           CH.sub.3                                                                               ##STR905##                                                 H           H                                                                                      ##STR906##                                                 F           H                                                                                      ##STR907##                                                 H           CH.sub.3                                                                               ##STR908##                                                 F           CH.sub.3                                                                               ##STR909##                                                 H           H                                                                                      ##STR910##                                                 F           H                                                                                      ##STR911##                                                 H           CH.sub.3                                                                               ##STR912##                                                 F           CH.sub.3                                                                               ##STR913##                                                 H           H                                                                                      ##STR914##                                                 F           H                                                                                      ##STR915##                                                 H           CH.sub.3                                                                               ##STR916##                                                 F           CH.sub.3                                                                               ##STR917##                                                 H           H                                                                                      ##STR918##                                                 F           H                                                                                      ##STR919##                                                 H           CH.sub.3                                                                               ##STR920##                                                 F           CH.sub.3                                                                               ##STR921##                                                 H           H                                                                                      ##STR922##                                                 F           H                                                                                      ##STR923##                                                 H           CH.sub.3                                                                               ##STR924##                                                 F           CH.sub.3                                                                               ##STR925##                                                 H           H                                                                                      ##STR926##                                                 F           H                                                                                      ##STR927##                                                 H           CH.sub.3                                                                               ##STR928##                                                 F           CH.sub.3                                                                               ##STR929##                                                 H           H                                                                                      ##STR930##                                                 F           H                                                                                      ##STR931##                                                 H           CH.sub.3                                                                               ##STR932##                                                 F           CH.sub.3                                                                               ##STR933##                                                 H           H                                                                                      ##STR934##                                                 F           H                                                                                      ##STR935##                                                 H           CH.sub.3                                                                               ##STR936##                                                 F           CH.sub.3                                                                               ##STR937##                                                 H           H                                                                                      ##STR938##                                                 F           H                                                                                      ##STR939##                                                 H           CH.sub.3                                                                               ##STR940##                                                 F           CH.sub.3                                                                               ##STR941##                                                 H           H                                                                                      ##STR942##                                                 F           H                                                                                      ##STR943##                                                 H           CH.sub.3                                                                               ##STR944##                                                 F           CH.sub.3                                                                               ##STR945##                                                 H           H                                                                                      ##STR946##                                                 F           H                                                                                      ##STR947##                                                 H           CH.sub.3                                                                               ##STR948##                                                 F           CH.sub.3                                                                               ##STR949##                                                 H           H                                                                                      ##STR950##                                                 F           H                                                                                      ##STR951##                                                 H           CH.sub.3                                                                               ##STR952##                                                 F           CH.sub.3                                                                               ##STR953##                                                 H           H                                                                                      ##STR954##                                                 F           H                                                                                      ##STR955##                                                 H           CH.sub.3                                                                               ##STR956##                                                 F           CH.sub.3                                                                               ##STR957##                                                 H           H                                                                                      ##STR958##                                                 F           H                                                                                      ##STR959##                                                 H           CH.sub.3                                                                               ##STR960##                                                 F           CH.sub.3                                                                               ##STR961##                                                 H           H                                                                                      ##STR962##                                                 F           H                                                                                      ##STR963##                                                 H           CH.sub.3                                                                               ##STR964##                                                 F           CH.sub.3                                                                               ##STR965##                                                 H           H                                                                                      ##STR966##                                                 F           H                                                                                      ##STR967##                                                 H           CH.sub.3                                                                               ##STR968##                                                 F           CH.sub.3                                                                               ##STR969##                                                 H           H                                                                                      ##STR970##                                                 F           H                                                                                      ##STR971##                                                 H           CH.sub.3                                                                               ##STR972##                                                 F           CH.sub.3                                                                               ##STR973##                                                 ______________________________________                                    

The N-aryltetrahydrophthalimide compounds I, or herbicidal agents containing them, may be applied for instance in the form of directly sprayable solutions, powders, suspensions (including high-percentage aqueous, oily or other suspensions), dispersions, emulsions, oil dispersions, pastes, dusts, broadcasting agents, or granules by spraying, atomizing, dusting, broadcasting or watering. The forms of application depend entirely on the purpose for which the agents are being used, but they must endure as fine a distribution of the active ingredients according to the invention as possible.

For the preparation of solutions, emulsions, pastes and oil dispersions to be sprayed direct, mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, further coal-tar oils, and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc. are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes, oil dispersions or wettable powders by adding water. To prepare emulsions, pastes and oil dispersions the ingredients as such or dissolved in an oil or solvent may be homogenized in water by means of wetting or dispersing agents, adherents or emulsifiers. Concentrates which are suitable for dilution with water may be prepared from active ingredient, wetting agent, adherent, emulsifying or dispersing agent and possibly solvent or oil.

Examples of surfactants are: alkali metal, alkaline earth metal and ammonium salts of ligninsulfonic acid, naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl sulfonates, alkyl sulfates, and alkyl sulfonates, alkali metal and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, alkali metal and alkaline earth metal salts of fatty acids, salts of sulfated hexadecanols, heptadecanols, and octadecanols, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, ethoxylated octylphenol and ethoxylated nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulfite waste liquors and methyl cellulose.

Powders, dusts and broadcasting agents may be prepared by mixing or grinding the active ingredients with a solid carrier.

Granules, e.g., coated, impregnated or homogeneous granules, may be prepared by bonding the active ingredients to solid carriers. Examples of solid carriers are mineral earths such as silicic acid, silica gels, silicates, talc, kaolin, attapulgus clay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and ureas, and vegetable products such as grain flours, bark meal, wood meal, and nutshell meal, cellulosic powders, etc.

The formulations contain from 0.1 to 95, and preferably 0.5 to 90, % by weight of active ingredient.

Examples of formulations are give below.

I. 90 parts by weight of compound no. 1.003 is mixed with 10 parts by weight of N-methyl-alpha-pyrrolidone. A mixture is obtained which is suitable for application in the form of very fine drops.

II. 20 parts by weight of compound no. 1.011 is dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzene-sulfonic acid, and 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

III. 20 parts by weight of compound no. 1.035 is dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide and 1 mole of isooctylphenol, and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

IV. 20 parts by weight of compound no. 3.059 is dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210° and 280° C., and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and uniformly distributing it therein, an aqueous dispersion is obtained containing 0.02% by weight of the active ingredient.

V. 20 parts by weight of compound no. 4.047 is well mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 17 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite water liquor, and 60 parts by weight of powdered silica gel, and triturated in a hammer mill. By uniformly distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained containing 0.1% by weight of the active ingredient.

VI. 3 parts by weight of compound no. 1.023 is intimately mixed with 97 parts by weight of particulate kaolin. A dust is obtained containing 3% by weight of the active ingredient.

VII. 30 parts by weight of the compound no. 1.033 is intimately mixed with a mixture consisting of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. A formulation of the active ingredient is obtained having good adherence.

VIII. 20 parts of compound no. 3.067 is intimately mixed with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.

The herbicidal agents, or the active ingredients on which they are based, may be applied pre- or postemergence. If certain crop plants tolerate the active ingredients less well, application techniques may be used in which the herbicidal agents are sprayed from suitable equipment in such a manner that the leaves of sensitive crop plants are if possible not touched, and the agents reach the soil or the unwanted plants growing beneath the crop plants (post-directed, lay-by treatment).

The application rates depend on the objective to be achieved, the time of the year, the plants to be combated and their growth stage, and are from 0.001 to 5.0, preferably 0.01 and 0.5, kg/ha.

In view of the number of application methods available the compounds according to the invention, or agents containing them, may be used in a further large number of crop plants for combating unwanted plants. Examples of such crops are as follows:

    ______________________________________                                         Botanical name          Common name                                            ______________________________________                                         Allium cepa             onions                                                 Ananas comosus          pineapples                                             Arachis hypogaea        peanuts                                                                        (groundnuts)                                           Asparagus officinalis   asparagus                                              Avena sativa            oats                                                   Beta vulgaris spp. altissima                                                                           sugarbeets                                             Beta vulgaris spp. rapa fodder beets                                           Beta vulgaris spp. esculenta                                                                           table beets,                                                                   red beets                                              Brassica napus var. napus                                                                              rapeseed                                               Brassica napus var. napobrassica                                                                       swedes                                                 Brassica napus var. rapa                                                                               turnips                                                Brassica rapa var. silvestris                                                  Camellia sinensis       tea plants                                             Carthamus tinctorius    safflower                                              Carya illinoinensis     pecan trees                                            Citrus limon            lemons                                                 Citrus maxima           grapefruits                                            Citrus reticulata       mandarins                                              Citrus sinensis         orange trees                                           Coffea arabica (Coffea canephora,                                                                      coffee plants                                          Coffea liberica)                                                               Cucumis melo            melons                                                 Cucumis sativus         cucumbers                                              Cynodon dactylon        Bermudagrass                                           Daucus carota           carrots                                                Elais guineensis        oil palms                                              Fragaria vesca          strawberries                                           Glycine max             soybeans                                               Gossypium hirsutum (Gossypium arboreum,                                                                cotton                                                 Gossypium herbaceum, Gossypium vitifolium)                                     Helianthus annuus       sunflowers                                             Helianthus tuberosus    Jerusalem                                                                      artichoke                                              Hevea brasiliensis      rubber plants                                          Hordeum vulgare         barley                                                 Humulus lupulus         hops                                                   Ipomoea batatas         sweet potatoes                                         Juglans regia           walnut trees                                           Lactuca sativa          lettuce                                                Lens culinaris          lentils                                                Linum usitatissimum     flax                                                   Lycopersicon lycopersicum                                                                              tomatoes                                               Malus spp.              apples trees                                           Manihot esculenta       cassava                                                Medicago sativa         alfalfa (lucerne)                                      Mentha piperita         peppermint                                             Musa spp.               banana plants                                          Nicotiana tabacum (N. rustica)                                                                         tobacco                                                Olea europaea           olive trees                                            Oryza sativa            rice                                                   Phaseolus lunatus       limabeans                                              Phaseolus mungo         mungbeans                                              Phaseolus vulgaris      snapbeans, green                                                               beans, dry beans                                       Pennisetum glaucum      pearl millet                                           Petroselinum crispum spp. tuberosum                                                                    parsley                                                Picea abies             Norway spruce                                          Abies alba              fir trees                                              Pinus spp.              pine trees                                             Pisum sativum           English peas                                           Prunus avium            cherry trees                                           Prunus domestica        plum trees                                             Prunus dulcis           almond trees                                           Prunus persica          peach trees                                            Pyrus communis          pear trees                                             Ribes sylvestre         redcurrants                                            Ribes uva-crispa        gooseberries                                           Ricinus communis        castor-oil plants                                      Saccharum officinarum   sugar cane                                             Secale cereale          rye                                                    Sesamum indicum         sesame                                                 Solanum tuberosum       Irish potatoes                                         Sorghum bicolor (s. vulgare)                                                                           sorghum                                                Sorghum dochna          sorgo                                                  Spinacia oleracea       spinach                                                Theobroma cacao         cacao plants                                           Trifolium pratense      red clover                                             Triticum aestivum       wheat                                                  Triticum durum          durum wheat                                            Vaccinium corymbosum    blueberries                                            Vaccinium vitis-idaea   cranberries                                            Vicia faba              tick beans                                             Vigna sinensis (V. unguiculata)                                                                        cow peas                                               Vitis vinifera          grapes                                                 Zea mays                Indian corn,                                                                   sweet corn, maize                                      ______________________________________                                    

To increase the spectrum of action and to achieve synergistic effects, the N-aryltetrahydrophthalimide compounds of the formula I may be mixed and applied together with numerous representatives of other herbicidal or growth-regulating active ingredient groups. Examples of suitable components are diazines, 4-H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenylcarbamates, thiolcarbamates, halocarboxylic acids, triazines, amides, ureas, diphenyl ethers, triazinones, uracils, benzofuran derivatives, cyclohexane-1,3-dione derivatives, quinolinecarboxylic acids, phenyloxy- or heteroaryloxy-phenylpropionic acids and salts, esters and amides thereof, etc.

It may also be useful to apply the novel compounds of the formula I, either alone or in combination with other herbicides, in admixture with other crop protection agents, e.g., agents for combating pests or phytopathogenic fungi or bacteria. The compounds of may also be mixed with solutions of mineral salts used to remedy nutritional or trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

SYNTHESIS EXAMPLES Example 1 ##STR974##

a) 4.9 g (0.03 mol) of 6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one is introduced into 50 ml of dimethylformamide. At 5° C., 0.79 g (0.033 mol) of sodium hydride is added, and the mixture is stirred for 30 minutes at this temperature. Subsequently, 5.9 g (0.033 mol) of 4-bromomethyltetrahydropyran is added, the mixture is stirred for 3 hours at 60° C., 200 ml of water is added, extraction is carried out twice with methylene chloride, followed by drying and evaporation of the solvent under reduced pressure. There is obtained 5 g (64%) of 4-(tetrahydropyran-4-ylmethyl)-6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-one as an oil.

b) 4.5 g (0.017 mol) of the abovementioned aniline and 2.7 g (0.018 mol) of cyclohexene-1,2-dicarboxylic anhydride are stirred for 3 hours at 70° C. in 70 ml of glacial acetic acid. After the mixture has cooled, 100 ml of water is added and the mixture filtered. The precipitate is washed with water and dried. There is obtained 3.5 g (52%) of N-[4-(tetrahydropyran-4-ylmethyl)-3,4-dihydro-2H-1,4-benzoxazin-3-on-6-yl]-3,4,5,6-tetrahydrophthalimide (m.p. 187°-189° C.) (Table 1, No. 1.033).

                  TABLE 1                                                          ______________________________________                                          ##STR975##                    I                                               No.   R.sup.1                                                                              R.sup.2 R.sup.3   R.sup.4                                                                               R.sup.5                                                                            m.p. [°C.]                     ______________________________________                                         1.001 H     H                                                                                       ##STR976##                                                                              H      H                                         1.002 F     H                                                                                       ##STR977##                                                                              H      H                                         1.003 H     H                                                                                       ##STR978##                                                                              H      H   165-166                               1.004 F     H                                                                                       ##STR979##                                                                              H      H   204-206                               1.005 H     H                                                                                       ##STR980##                                                                              CH.sub.3                                                                              H                                         1.006 F     H                                                                                       ##STR981##                                                                              CH.sub.3                                                                              H                                         1.007 H     H                                                                                       ##STR982##                                                                              H      H                                         1.008 F     H                                                                                       ##STR983##                                                                              H      H                                         1.009 H     H                                                                                       ##STR984##                                                                              H      H                                         1.010 F     H                                                                                       ##STR985##                                                                              H      H                                         1.011 H     H                                                                                       ##STR986##                                                                              H      H   140-142                               1.012 F     H                                                                                       ##STR987##                                                                              H      H                                         1.013 H     H                                                                                       ##STR988##                                                                              CH.sub.3                                                                              H                                         1.014 F     H                                                                                       ##STR989##                                                                              CH.sub.3                                                                              H                                         1.015 H     H                                                                                       ##STR990##                                                                              H      H                                         1.016 F     H                                                                                       ##STR991##                                                                              H      H                                         1.017 H     H                                                                                       ##STR992##                                                                              H      H                                         1.018 F     H                                                                                       ##STR993##                                                                              H      H                                         1.019 H     H                                                                                       ##STR994##                                                                              H      H                                         1.020 F     H                                                                                       ##STR995##                                                                              H      H                                         1.021 H     H                                                                                       ##STR996##                                                                              H      H                                         1.022 F     H                                                                                       ##STR997##                                                                              H      H                                         1.023 H     H                                                                                       ##STR998##                                                                              H      H   145-147                               1.024 F     H                                                                                       ##STR999##                                                                              H      H                                         1.025 H     H                                                                                       ##STR1000##                                                                             CH.sub.3                                                                              H                                         1.026 F     H                                                                                       ##STR1001##                                                                             CH.sub.3                                                                              H                                         1.027 H     H                                                                                       ##STR1002##                                                                             H      H   138-140                               1.028 F     H                                                                                       ##STR1003##                                                                             H      H   70 (Zers.)                            1.029 H     H                                                                                       ##STR1004##                                                                             CH.sub.3                                                                              H   145-147                               1.030 F     H                                                                                       ##STR1005##                                                                             CH.sub.3                                                                              H                                         1.031 H     CH.sub.3                                                                                ##STR1006##                                                                             H      H                                         1.032 F     CH.sub.3                                                                                ##STR1007##                                                                             H      H                                         1.033 H     H                                                                                       ##STR1008##                                                                             H      H   187-189                               1.034 F     H                                                                                       ##STR1009##                                                                             H      H                                         1.035 H     H                                                                                       ##STR1010##                                                                             CH.sub.3                                                                              H   150-152                               1.036 F     H                                                                                       ##STR1011##                                                                             CH.sub.3                                                                              H                                         1.037 H     H                                                                                       ##STR1012##                                                                             H      H                                         1.038 F     H                                                                                       ##STR1013##                                                                             H      H                                         1.039 H     H                                                                                       ##STR1014##                                                                             H      H                                         1.040 F     H                                                                                       ##STR1015##                                                                             H      H   178-179                               1.041 H     H                                                                                       ##STR1016##                                                                             CH.sub.3                                                                              H                                         1.042 F     H                                                                                       ##STR1017##                                                                             CH.sub.3                                                                              H                                         1.043 H     H                                                                                       ##STR1018##                                                                             H      H                                         1.044 F     H                                                                                       ##STR1019##                                                                             H      H                                         1.045 H     H                                                                                       ##STR1020##                                                                             H      H                                         1.046 F     H                                                                                       ##STR1021##                                                                             H      H                                         1.047 H     H                                                                                       ##STR1022##                                                                             H      H                                         1.048 F     H                                                                                       ##STR1023##                                                                             H      H                                         1.049 H     H                                                                                       ##STR1024##                                                                             H      H   127-129                               1.050 F     H                                                                                       ##STR1025##                                                                             H      H                                         1.051 H     H                                                                                       ##STR1026##                                                                             H      H                                         1.052 F     H                                                                                       ##STR1027##                                                                             H      H                                         1.053 H     H                                                                                       ##STR1028##                                                                             H      H   178-180                               1.054 F     H                                                                                       ##STR1029##                                                                             H      H                                         1.055 H     H                                                                                       ##STR1030##                                                                             H      H   157-158                               1.056 F     H                                                                                       ##STR1031##                                                                             H      H                                         1.057 H     H                                                                                       ##STR1032##                                                                             H      H   177-178                               1.058 F     H                                                                                       ##STR1033##                                                                             H      H                                         ______________________________________                                    

                  TABLE 2                                                          ______________________________________                                          ##STR1034##                   I                                               No.  R.sup.1 R.sup.2                                                                               R.sup.3    R.sup.4                                                                              R.sup.5                                                                             m.p. [°C.]                    ______________________________________                                         2.001                                                                               H       H                                                                                      ##STR1035##                                                                              H     H                                         2.002                                                                               F       H                                                                                      ##STR1036##                                                                              H     H                                         2.003                                                                               H       H                                                                                      ##STR1037##                                                                              H     H                                         2.004                                                                               F       H                                                                                      ##STR1038##                                                                              H     H                                         2.005                                                                               H       H                                                                                      ##STR1039##                                                                              CH.sub.3                                                                             H                                         2.006                                                                               F       H                                                                                      ##STR1040##                                                                              CH.sub.3                                                                             H                                         2.007                                                                               H       H                                                                                      ##STR1041##                                                                              H     H                                         2.008                                                                               F       H                                                                                      ##STR1042##                                                                              H     H                                         2.009                                                                               H       H                                                                                      ##STR1043##                                                                              H     H                                         2.010                                                                               F       H                                                                                      ##STR1044##                                                                              H     H                                         2.011                                                                               H       H                                                                                      ##STR1045##                                                                              H     H                                         2.012                                                                               F       H                                                                                      ##STR1046##                                                                              H     H                                         2.013                                                                               H       H                                                                                      ##STR1047##                                                                              CH.sub.3                                                                             H                                         2.014                                                                               F       H                                                                                      ##STR1048##                                                                              CH.sub.3                                                                             H                                         2.015                                                                               H       H                                                                                      ##STR1049##                                                                              H     H                                         2.016                                                                               F       H                                                                                      ##STR1050##                                                                              H     H                                         2.017                                                                               H       H                                                                                      ##STR1051##                                                                              H     H                                         2.018                                                                               F       H                                                                                      ##STR1052##                                                                              H     H                                         2.019                                                                               H       H                                                                                      ##STR1053##                                                                              H     H                                         2.020                                                                               F       H                                                                                      ##STR1054##                                                                              H     H                                         2.021                                                                               H       H                                                                                      ##STR1055##                                                                              H     H                                         2.022                                                                               F       H                                                                                      ##STR1056##                                                                              H     H                                         2.023                                                                               H       H                                                                                      ##STR1057##                                                                              H     H                                         2.024                                                                               F       H                                                                                      ##STR1058##                                                                              H     H                                         2.025                                                                               H       H                                                                                      ##STR1059##                                                                              CH.sub.3                                                                             H                                         2.026                                                                               F       H                                                                                      ##STR1060##                                                                              CH.sub.3                                                                             H                                         2.027                                                                               H       H                                                                                      ##STR1061##                                                                              H     H                                         2.028                                                                               F       H                                                                                      ##STR1062##                                                                              H     H                                         2.029                                                                               H       H                                                                                      ##STR1063##                                                                              CH.sub.3                                                                             H                                         2.030                                                                               F       H                                                                                      ##STR1064##                                                                              CH.sub.3                                                                             H                                         2.031                                                                               H       CH.sub.3                                                                               ##STR1065##                                                                              H     H                                         2.032                                                                               F       CH.sub.3                                                                               ##STR1066##                                                                              H     H                                         2.033                                                                               H       H                                                                                      ##STR1067##                                                                              H     H                                         2.034                                                                               F       H                                                                                      ##STR1068##                                                                              H     H                                         2.035                                                                               H       H                                                                                      ##STR1069##                                                                              CH.sub.3                                                                             H                                         2.036                                                                               F       H                                                                                      ##STR1070##                                                                              CH.sub.3                                                                             H                                         2.037                                                                               H       H                                                                                      ##STR1071##                                                                              H     H                                         2.038                                                                               F       H                                                                                      ##STR1072##                                                                              H     H                                         2.039                                                                               H       H                                                                                      ##STR1073##                                                                              H     H                                         2.040                                                                               F       H                                                                                      ##STR1074##                                                                              H     H                                         2.041                                                                               H       H                                                                                      ##STR1075##                                                                              CH.sub.3                                                                             H                                         2.042                                                                               F       H                                                                                      ##STR1076##                                                                              CH.sub.3                                                                             H                                         2.043                                                                               H       H                                                                                      ##STR1077##                                                                              H     H                                         2.044                                                                               F       H                                                                                      ##STR1078##                                                                              H     H                                         2.045                                                                               H       H                                                                                      ##STR1079##                                                                              H     H                                         2.046                                                                               F       H                                                                                      ##STR1080##                                                                              H     H                                         2.047                                                                               H       H                                                                                      ##STR1081##                                                                              H     H                                         2.048                                                                               F       H                                                                                      ##STR1082##                                                                              H     H                                         2.049                                                                               H       H                                                                                      ##STR1083##                                                                              H     H                                         2.050                                                                               F       H                                                                                      ##STR1084##                                                                              H     H                                         2.051                                                                               H       H                                                                                      ##STR1085##                                                                              H     H                                         2.052                                                                               F       H                                                                                      ##STR1086##                                                                              H     H                                         2.053                                                                               H       H                                                                                      ##STR1087##                                                                              H     H                                         2.054                                                                               F       H                                                                                      ##STR1088##                                                                              H     H                                         2.055                                                                               H       H                                                                                      ##STR1089##                                                                              H     H                                         2.056                                                                               F       H                                                                                      ##STR1090##                                                                              H     H                                         2.057                                                                               H       H                                                                                      ##STR1091##                                                                              H     H                                         2.058                                                                               F       H                                                                                      ##STR1092##                                                                              H     H                                         ______________________________________                                    

                  TABLE 2a                                                         ______________________________________                                          ##STR1093##                   I                                               No.  R.sup.1 A               R.sup.4                                                                             R.sup.5                                                                              m.p. [°C.]                      ______________________________________                                         2.059                                                                               H       H               H    H     230-231                                2.060                                                                               F       H               H    H                                            2.061                                                                               H       CH.sub.3        H    H                                            2.062                                                                               F       CH.sub.3        H    H                                            2.063                                                                               H       CH.sub.2 CH.sub.3                                                                              H    H                                            2.064                                                                               F       CH.sub.2 CH.sub.3                                                                              H    H                                            2.065                                                                               H       CH(CH.sub.3).sub.2                                                                             H                                                 2.066                                                                               F       CH(CH.sub.3).sub.2                                                                             H    H                                            2.067                                                                               H       CH.sub.2 CHCH.sub.2                                                                            H    H                                            2.068                                                                               F       CH.sub.2 CHCH.sub.2                                                                            H    H                                            2.069                                                                               H       CH.sub.2 CCH    H    H     193-194                                2.070                                                                               F       CH.sub.2 C CH   H    H                                            2.071                                                                               H       CH.sub.2 OCH.sub.3                                                                             H    H                                            2.072                                                                               F       CH.sub.2 OCH.sub.3                                                                             H    H                                            2.073                                                                               H       CH.sub.2 CH.sub.2 OCH.sub.3                                                                    H    H                                            2.074                                                                               F       CH.sub.2 CH.sub.2 OCH.sub.3                                                                    H    H                                            2.075                                                                               H       CH.sub.2 CO.sub.2 CH.sub.3                                                                     H    H                                            2.076                                                                               F       CH.sub.2 CO.sub.2 CH.sub.3                                                                     H    H                                            2.077                                                                               H       CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                            H    H                                            2.078                                                                               F       CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                            H    H                                            2.079                                                                               H       CH(CH.sub.3)CO.sub.2 CH.sub.3                                                                  H    H                                            2.080                                                                               F       CH(CH.sub.3)CO.sub.2 CH.sub.3                                                                  H    H                                            2.081                                                                               H       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         H    H                                            2.082                                                                               F       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         H    H                                            2.083                                                                               H       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         CH.sub.3                                                                            H                                            2.084                                                                               F       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         CH.sub.3                                                                            H                                            2.085                                                                               H       CH.sub.2 CHCH.sub.2                                                                            CH.sub.3                                                                            H                                            2.086                                                                               F       CH.sub.2 CHCH.sub.2                                                                            CH.sub.3                                                                            H                                            2.087                                                                               H       CH.sub.2 CCH    CH.sub.3                                                                            H                                            2.088                                                                               F       CH.sub.2 C CH   CH.sub.3                                                                            H                                            ______________________________________                                    

                  TABLE 3                                                          ______________________________________                                          ##STR1094##                   I                                               No.  R.sup.1 R.sup.2                                                                               R.sup.3    R.sup.4                                                                              R.sup.5                                                                             m.p. [°C.]                    ______________________________________                                         3.001                                                                               H       H                                                                                      ##STR1095##                                                                              H     H                                         3.002                                                                               F       H                                                                                      ##STR1096##                                                                              H     H                                         3.003                                                                               H       H                                                                                      ##STR1097##                                                                              H     H                                         3.004                                                                               F       H                                                                                      ##STR1098##                                                                              H     H                                         3.005                                                                               H       H                                                                                      ##STR1099##                                                                              CH.sub.3                                                                             H                                         3.006                                                                               F       H                                                                                      ##STR1100##                                                                              CH.sub.3                                                                             H                                         3.007                                                                               H       H                                                                                      ##STR1101##                                                                              H     H                                         3.008                                                                               F       H                                                                                      ##STR1102##                                                                              H     H                                         3.009                                                                               H       H                                                                                      ##STR1103##                                                                              H     H                                         3.010                                                                               F       H                                                                                      ##STR1104##                                                                              H     H                                         3.011                                                                               H       H                                                                                      ##STR1105##                                                                              H     H    147-149                              3.012                                                                               F       H                                                                                      ##STR1106##                                                                              H     H                                         3.013                                                                               H       H                                                                                      ##STR1107##                                                                              CH.sub.3                                                                             H                                         3.014                                                                               F       H                                                                                      ##STR1108##                                                                              CH.sub.3                                                                             H                                         3.015                                                                               H       H                                                                                      ##STR1109##                                                                              H     H                                         3.016                                                                               F       H                                                                                      ##STR1110##                                                                              H     H                                         3.017                                                                               H       H                                                                                      ##STR1111##                                                                              H     H                                         3.018                                                                               F       H                                                                                      ##STR1112##                                                                              H     H                                         3.019                                                                               H       H                                                                                      ##STR1113##                                                                              H     H                                         3.020                                                                               F       H                                                                                      ##STR1114##                                                                              H     H                                         3.021                                                                               H       H                                                                                      ##STR1115##                                                                              H     H                                         3.022                                                                               F       H                                                                                      ##STR1116##                                                                              H     H                                         3.023                                                                               H       H                                                                                      ##STR1117##                                                                              H     H                                         3.024                                                                               F       H                                                                                      ##STR1118##                                                                              H     H                                         3.025                                                                               H       H                                                                                      ##STR1119##                                                                              CH.sub.3                                                                             H                                         3.026                                                                               F       H                                                                                      ##STR1120##                                                                              CH.sub.3                                                                             H                                         3.027                                                                               H       H                                                                                      ##STR1121##                                                                              H     H    188-190                              3.028                                                                               F       H                                                                                      ##STR1122##                                                                              H     H                                         3.029                                                                               H       H                                                                                      ##STR1123##                                                                              CH.sub.3                                                                             H                                         3.030                                                                               F       H                                                                                      ##STR1124##                                                                              CH.sub.3                                                                             H                                         3.031                                                                               H       CH.sub.3                                                                               ##STR1125##                                                                              H     H                                         3.032                                                                               F       CH.sub.3                                                                               ##STR1126##                                                                              H     H                                         3.033                                                                               H       H                                                                                      ##STR1127##                                                                              H     H                                         3.034                                                                               F       H                                                                                      ##STR1128##                                                                              H     H                                         3.035                                                                               H       H                                                                                      ##STR1129##                                                                              CH.sub.3                                                                             H                                         3.036                                                                               F       H                                                                                      ##STR1130##                                                                              CH.sub.3                                                                             H                                         3.037                                                                               H       H                                                                                      ##STR1131##                                                                              H     H                                         3.038                                                                               F       H                                                                                      ##STR1132##                                                                              H     H                                         3.039                                                                               H       H                                                                                      ##STR1133##                                                                              H     H                                         3.040                                                                               F       H                                                                                      ##STR1134##                                                                              H     H                                         3.041                                                                               H       H                                                                                      ##STR1135##                                                                              CH.sub.3                                                                             H                                         3.042                                                                               F       H                                                                                      ##STR1136##                                                                              CH.sub.3                                                                             H                                         3.043                                                                               H       H                                                                                      ##STR1137##                                                                              H     H                                         3.044                                                                               F       H                                                                                      ##STR1138##                                                                              H     H                                         3.045                                                                               H       H                                                                                      ##STR1139##                                                                              H     H                                         3.046                                                                               F       H                                                                                      ##STR1140##                                                                              H     H                                         3.047                                                                               H       H                                                                                      ##STR1141##                                                                              H     H                                         3.048                                                                               F       H                                                                                      ##STR1142##                                                                              H     H                                         3.049                                                                               H       H                                                                                      ##STR1143##                                                                              H     H                                         3.050                                                                               F       H                                                                                      ##STR1144##                                                                              H     H                                         3.051                                                                               H       H                                                                                      ##STR1145##                                                                              H     H                                         3.052                                                                               F       H                                                                                      ##STR1146##                                                                              H     H                                         3.053                                                                               H       H                                                                                      ##STR1147##                                                                              H     H                                         3.054                                                                               F       H                                                                                      ##STR1148##                                                                              H     H                                         3.055                                                                               H       H                                                                                      ##STR1149##                                                                              H     H    173-175                              3.056                                                                               F       H                                                                                      ##STR1150##                                                                              H     H                                         3.057                                                                               H       H                                                                                      ##STR1151##                                                                              H     H                                         3.058                                                                               F       H                                                                                      ##STR1152##                                                                              H     H                                         ______________________________________                                    

                  TABLE 3a                                                         ______________________________________                                          ##STR1153##                   I                                               No.  R.sup.1 A               R.sup.4                                                                             R.sup.5                                                                              m.p. [°C.]                      ______________________________________                                         3.059                                                                               H       H               H    H     237-238                                3.060                                                                               F       H               H    H                                            3.061                                                                               H       CH.sub.3        H    H     232-234                                3.062                                                                               F       CH.sub.3        H    H                                            3.063                                                                               H       CH.sub.2 CH.sub.3                                                                              H    H                                            3.064                                                                               F       CH.sub.2 CH.sub.3                                                                              H    H                                            3.065                                                                               H       CH(CH.sub.3).sub.2                                                                             H    H                                            3.066                                                                               F       CH(CH.sub.3).sub.2                                                                             H    H                                            3.067                                                                               H       CH.sub.2 CHCH.sub.2                                                                            H    H     168-170                                3.068                                                                               F       CH.sub.2 CHCH.sub.2                                                                            H    H                                            3.069                                                                               H       CH.sub.2 CCH    H    H     196-198                                3.070                                                                               F       CH.sub.2 C CH   H    H                                            3.071                                                                               H       CH.sub.2 OCH.sub.3                                                                             H    H                                            3.072                                                                               F       CH.sub.2 OCH.sub.3                                                                             H    H                                            3.073                                                                               H       CH.sub.2 CH.sub.2 OCH.sub.3                                                                    H    H                                            3.074                                                                               F       CH.sub.2 CH.sub.2 OCH.sub.3                                                                    H    H                                            3.075                                                                               H       CH.sub.2 CO.sub.2 CH.sub.3                                                                     H    H                                            3.076                                                                               F       CH.sub.2 CO.sub.2 CH.sub.3                                                                     H    H                                            3.077                                                                               H       CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                            H    H                                            3.078                                                                               F       CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                                                            H    H                                            3.079                                                                               H       CH(CH.sub.3)CO.sub.2 CH.sub.3                                                                  H    H                                            3.080                                                                               F       CH(CH.sub.3)CO.sub.2 CH.sub.3                                                                  H    H                                            3.081                                                                               H       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         H    H                                            3.082                                                                               F       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         H    H                                            3.083                                                                               H       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         CH.sub.3                                                                            H                                            3.084                                                                               F       CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                                                         CH.sub.3                                                                            H                                            3.085                                                                               H       CH.sub.2 CHCH.sub.2                                                                            CH.sub.3                                                                            H                                            3.086                                                                               F       CH.sub.2 CHCH.sub.2                                                                            CH.sub.3                                                                            H                                            3.087                                                                               H       CH.sub.2 CCH    CH.sub.3                                                                            H                                            3.088                                                                               F       CH.sub.2 CCH    CH.sub.3                                                                            H                                            ______________________________________                                    

                  TABLE 4                                                          ______________________________________                                          ##STR1154##                   I                                               No.    R.sup.1   R.sup.2  R.sup.3  m.p. [°C.]                           ______________________________________                                         4.001  H         H                                                                                        ##STR1155##                                         4.002  F         H                                                                                        ##STR1156##                                         4.003  H         H                                                                                        ##STR1157##                                         4.004  F         H                                                                                        ##STR1158##                                         4.005  H         H                                                                                        ##STR1159##                                         4.006  F         H                                                                                        ##STR1160##                                         4.007  H         H                                                                                        ##STR1161##                                         4.008  F         H                                                                                        ##STR1162##                                         4.009  H         H                                                                                        ##STR1163##                                         4.010  F         H                                                                                        ##STR1164##                                         4.011  H         H                                                                                        ##STR1165##                                         4.012  F         H                                                                                        ##STR1166##                                         4.013  H         H                                                                                        ##STR1167##                                         4.014  F         H                                                                                        ##STR1168##                                         4.015  H         H                                                                                        ##STR1169##                                         4.016  H         H                                                                                        ##STR1170##                                         4.017  H         H                                                                                        ##STR1171##                                         4.018  F         H                                                                                        ##STR1172##                                         4.019  H         H                                                                                        ##STR1173##                                         4.020  F         H                                                                                        ##STR1174##                                         4.021  H         H                                                                                        ##STR1175##                                                                            150-152                                     4.022  F         H                                                                                        ##STR1176##                                         4.023  H         CH.sub.3                                                                                 ##STR1177##                                         4.024  F         CH.sub.3                                                                                 ##STR1178##                                         4.025  H         H                                                                                        ##STR1179##                                         4.026  F         H                                                                                        ##STR1180##                                         4.027  H         H                                                                                        ##STR1181##                                         4.028  F         H                                                                                        ##STR1182##                                         4.029  H         H                                                                                        ##STR1183##                                         4.030  F         H                                                                                        ##STR1184##                                         4.031  H         H                                                                                        ##STR1185##                                         4.032  F         H                                                                                        ##STR1186##                                         4.033  H         H                                                                                        ##STR1187##                                         4.034  F         H                                                                                        ##STR1188##                                         4.035  H         H                                                                                        ##STR1189##                                         4.036  F         H                                                                                        ##STR1190##                                         4.037  H         H                                                                                        ##STR1191##                                         4.038  F         H                                                                                        ##STR1192##                                         4.039  H         H                                                                                        ##STR1193##                                         4.040  F         H                                                                                        ##STR1194##                                         4.041  H         H                                                                                        ##STR1195##                                         4.042  F         H                                                                                        ##STR1196##                                         4.043  H         H                                                                                        ##STR1197##                                         4.044  F         H                                                                                        ##STR1198##                                         4.045  H         H                                                                                        ##STR1199##                                         4.046  F         H                                                                                        ##STR1200##                                         ______________________________________                                    

                  TABLE 4a                                                         ______________________________________                                          ##STR1201##                   I                                               No.    R.sup.1   A              m.p. [°C.]                              ______________________________________                                         4.047  H         H              140-142                                        4.048  F         H                                                             4.049  H         CH.sub.3       205-207                                        4.050  F         CH.sub.3                                                      4.051  H         CH.sub.2 CH.sub.3                                             4.052  F         CH.sub.2 CH.sub.3                                             4.053  H         CH(CH.sub.3).sub.2                                            4.054  F         CH(CH.sub.3).sub.2                                            4.055  H         CH.sub.2 CHCH.sub.2                                           4.056  F         CH.sub.2 CHCH.sub.2                                           4.057  H         CH.sub.2 CCH                                                  4.058  F         CH.sub.2 CCH                                                  4.059  H         CH.sub.2 OCH.sub.3                                            4.060  F         CH.sub.2 OCH.sub.3                                            4.061  H         CH.sub.2 CH.sub.2 OCH.sub.3                                   4.062  F         CH.sub.2 CH.sub.2 OCH.sub.3                                   4.063  H         CH.sub.2 CO.sub.2 CH.sub.3                                    4.064  F         CH.sub.2 CO.sub.2 CH.sub.3                                    4.065  H         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                           4.066  F         CH.sub.2 CO.sub.2 CH.sub.2 CH.sub.3                           4.067  H         CH(CH.sub.3)CO.sub.2 CH.sub.3                                 4.068  F         CH(CH.sub.3)CO.sub.2 CH.sub.3                                 4.069  H         CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                        4.070  F         CH(CH.sub.3)CO.sub.2 CH.sub.2 CH.sub.3                        ______________________________________                                    

                  TABLE 5                                                          ______________________________________                                          ##STR1202##                   I                                               No.      R.sup.1                                                                              R.sup.2   R.sup.3   m.p. [°C.]                           ______________________________________                                         5.001    H     H                                                                                         ##STR1203##                                          5.002    F     H                                                                                         ##STR1204##                                          5.003    H     H                                                                                         ##STR1205##                                          5.004    F     H                                                                                         ##STR1206##                                          5.005    H     H                                                                                         ##STR1207##                                          5.006    F     H                                                                                         ##STR1208##                                          5.007    H     H                                                                                         ##STR1209##                                          5.008    F     H                                                                                         ##STR1210##                                          5.009    H     H                                                                                         ##STR1211##                                                                             147-151                                     5.010    F     H                                                                                         ##STR1212##                                          5.011    H     H                                                                                         ##STR1213##                                          5.012    F     H                                                                                         ##STR1214##                                          5.013    H     H                                                                                         ##STR1215##                                          5.014    F     H                                                                                         ##STR1216##                                          5.015    H     H                                                                                         ##STR1217##                                          5.016    F     H                                                                                         ##STR1218##                                          5.017    H     H                                                                                         ##STR1219##                                          5.018    F     H                                                                                         ##STR1220##                                          5.019    H     H                                                                                         ##STR1221##                                                                             133-135                                     5.020    F     H                                                                                         ##STR1222##                                          5.021    H     H                                                                                         ##STR1223##                                                                             167-169                                     5.022    F     H                                                                                         ##STR1224##                                          5.023    H     CH.sub.3                                                                                  ##STR1225##                                          5.024    F     CH.sub.3                                                                                  ##STR1226##                                          5.025    H     H                                                                                         ##STR1227##                                          5.026    F     H                                                                                         ##STR1228##                                          5.027    H     H                                                                                         ##STR1229##                                          5.028    F     H                                                                                         ##STR1230##                                          5.029    H     H                                                                                         ##STR1231##                                          5.030    F     H                                                                                         ##STR1232##                                          5.031    H     H                                                                                         ##STR1233##                                          5.032    F     H                                                                                         ##STR1234##                                          5.033    H     H                                                                                         ##STR1235##                                          5.034    F     H                                                                                         ##STR1236##                                          5.035    H     H                                                                                         ##STR1237##                                          5.036    F     H                                                                                         ##STR1238##                                          5.037    H     H                                                                                         ##STR1239##                                          5.038    F     H                                                                                         ##STR1240##                                          5.039    H     H                                                                                         ##STR1241##                                          5.040    F     H                                                                                         ##STR1242##                                          5.041    H     H                                                                                         ##STR1243##                                                                             206-207                                     5.042    F     H                                                                                         ##STR1244##                                          5.043    H     H                                                                                         ##STR1245##                                          5.044    F     H                                                                                         ##STR1246##                                          5.045    H     H                                                                                         ##STR1247##                                          5.046    F     H                                                                                         ##STR1248##                                          ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                          ##STR1249##                   I                                               No.      R.sup.1                                                                              R.sup.2   R.sup.3   m.p. [°C.]                           ______________________________________                                         6.001    H     H                                                                                         ##STR1250##                                          6.002    F     H                                                                                         ##STR1251##                                          6.003    H     H                                                                                         ##STR1252##                                          6.004    F     H                                                                                         ##STR1253##                                          6.005    H     H                                                                                         ##STR1254##                                          6.006    F     H                                                                                         ##STR1255##                                          6.007    H     H                                                                                         ##STR1256##                                          6.008    F     H                                                                                         ##STR1257##                                          6.009    H     H                                                                                         ##STR1258##                                          6.010    F     H                                                                                         ##STR1259##                                          6.011    H     H                                                                                         ##STR1260##                                          6.012    F     H                                                                                         ##STR1261##                                          6.013    H     H                                                                                         ##STR1262##                                          6.014    F     H                                                                                         ##STR1263##                                          6.015    H     H                                                                                         ##STR1264##                                          6.016    F     H                                                                                         ##STR1265##                                          6.017    H     H                                                                                         ##STR1266##                                          6.018    F     H                                                                                         ##STR1267##                                          6.019    H     H                                                                                         ##STR1268##                                          6.020    F     H                                                                                         ##STR1269##                                          6.021    H     H                                                                                         ##STR1270##                                          6.022    F     H                                                                                         ##STR1271##                                          6.023    H     CH.sub.3                                                                                  ##STR1272##                                          6.024    F     CH.sub.3                                                                                  ##STR1273##                                          6.025          H                                                                                         ##STR1274##                                          6.026    F     H                                                                                         ##STR1275##                                          6.027    H     H                                                                                         ##STR1276##                                          6.028    F     H                                                                                         ##STR1277##                                          6.029    H     H                                                                                         ##STR1278##                                          6.030    F     H                                                                                         ##STR1279##                                                                             187-189                                     6.031    H     H                                                                                         ##STR1280##                                          6.032    F     H                                                                                         ##STR1281##                                          6.033    H     H                                                                                         ##STR1282##                                          6.034    F     H                                                                                         ##STR1283##                                          6.035    H     H                                                                                         ##STR1284##                                          6.036    F     H                                                                                         ##STR1285##                                          6.037    H     H                                                                                         ##STR1286##                                          6.038    F     H                                                                                         ##STR1287##                                          6.039    H     H                                                                                         ##STR1288##                                          6.040    F     H                                                                                         ##STR1289##                                          6.041    H     H                                                                                         ##STR1290##                                          6.042    F     H                                                                                         ##STR1291##                                          6.043    H     H                                                                                         ##STR1292##                                          6.044    F     H                                                                                         ##STR1293##                                          6.045    H     H                                                                                         ##STR1294##                                          6.046    F     H                                                                                         ##STR1295##                                          ______________________________________                                    

USE EXAMPLES

The action of the N-aryltetrahydrophthalimide compounds of the formula I on plant growth is demonstrated by the following greenhouse experiments:

The vessels employed were plastic flowerpots having a volume of 300 cm³ and filled with a sandy loam containing about 0.3% humus. The seeds of the test plants were sown separately, according to species.

For the postemergence treatment, either plants which had been sown in the pots and grown there were selected, or they were cultivated separately as seedlings and transplanted to the pots a few days before being treated.

Depending on growth form, the plants were grown to a height of from 3 to 15 cm before being treated with the active ingredients which were suspended or emulsified in water and sprayed through finely distributing nozzles. The application rates for postemergence treatment were 0.06 and 0.125 kg of active ingredient per hectare.

The pots are set up in the greenhouse, species from warmer climates in warmer areas (20° to 35° C.) and species from moderate climates at 10° to 20° C. The experiments were run for from 2 to 4 weeks. During this time the plants were tended and their reactions to the various treatments assessed.

The assessment scale was 0 to 100, 100 denoting nonemergence or complete destruction of at least the visible plant parts, and 0 denoting no damage or normal growth.

The plants used in the greenhouse experiments were: Amaranthus retroflexus, Galium aparine, Stellaria media, Veronica spp., Oryza sativa, Solanum nigrum, and Triticum aestivum.

The compounds 1.027 and 1.029, applied postemergence at rates of 0.06 and 0.125 kg/ha, gave excellent control of unwanted broadleaved plants, and were well tolerated by rice and wheat. Compound 3.067, applied postemergence at a rate of 0.06 kg/ha, combated unwanted broadleaved plants without causing any appreciable damage to rice. 

We claim:
 1. An N-aryltetrahydrophthalimide compound of the formula I ##STR1296## where the substituents and indices have the following meanings: n is 0 or 1, R¹ is hydrogen or halogen, Y is --O--CR⁴ R⁵, R⁴ and R⁵ independently of one another being hydrogen or C₁ -C₃ -alkyl, R² is hydrogen or C₁ -C₃ -alkyl, R³ is a saturated or monounsaturated 5-membered or 6-membered ring made up of carbon atoms and one oxygen or sulfur atom which ring may be monosubstituted to trisubstituted by C₁ -C₃ -alkyl, or R³ is phenyl which is unsubstituted by monosubstituted or trisubstituted by at least one of the following: C₁ - or C₂ -alkyl, halogen, methoxy, nitro, or cyano, with the proviso that when n is 1, R³ is not phenyl or substituted phenyl.
 2. A herbicide containing an effective amount of a N-aryltetrahydrophthalimide compound of the formula I as defined in claim 1 and inert additives.
 3. A herbicide as defined in claim 2, containing an effective amount of a N-aryltetrahydrophthalimide compound of the formula I and further active constituents.
 4. A method for controlling undesirable plant growth, wherein the undesirable plants, their habitat, or both the undesired plants and their habitat are treated with a herbicidally effective amount of an N-aryltetrahydrophthalimide compound I, as defined in claim
 1. 